JPS5925788B2 - Ｎ−置換オキサゾリジン類の製法 - Google Patents

Ｎ−置換オキサゾリジン類の製法

Info

Publication number: JPS5925788B2
Authority: JP; Japan
Prior art keywords: formula; oxazolidine; group; item; general formula
Prior art date: 1975-08-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP51100109A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5236662A (en

Inventor

ハロルド・マホンライ・ピツト

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Stauffer Chemical Co

Original Assignee

Stauffer Chemical Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-08-28

Filing date

1976-08-21

Publication date

1984-06-21

1976-08-21 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1977-03-22 Publication of JPS5236662A publication Critical patent/JPS5236662A/ja

1984-06-21 Publication of JPS5925788B2 publication Critical patent/JPS5925788B2/ja

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 36
-1 N-substituted oxazolidines Chemical class 0.000 title claims description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
229910000039 hydrogen halide Inorganic materials 0.000 claims description 20
239000012433 hydrogen halide Substances 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 7
YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical group CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 6
150000008044 alkali metal hydroxides Chemical group 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
238000006482 condensation reaction Methods 0.000 claims description 3
SXSNYZPSATVORJ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-yl)ethanone Chemical group C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CC=C1 SXSNYZPSATVORJ-UHFFFAOYSA-N 0.000 claims description 2
230000000717 retained effect Effects 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims 5
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 3
RLJHUAABUCHYNU-UHFFFAOYSA-N 2,2-dichloro-1-(1,3-oxazolidin-3-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC1 RLJHUAABUCHYNU-UHFFFAOYSA-N 0.000 claims 2
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
KMDUXADUKNTNFV-UHFFFAOYSA-N 2,2-dichloro-1-(1,3-oxazolidin-2-yl)ethanone Chemical compound ClC(Cl)C(=O)C1NCCO1 KMDUXADUKNTNFV-UHFFFAOYSA-N 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
239000000047 product Substances 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 17
239000000370 acceptor Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
150000002917 oxazolidines Chemical class 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000007795 chemical reaction product Substances 0.000 description 12
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 9
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
238000000746 purification Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
125000004183 alkoxy alkyl group Chemical group 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
239000002253 acid Substances 0.000 description 5
125000001188 haloalkyl group Chemical group 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
239000002262 Schiff base Substances 0.000 description 4
150000004753 Schiff bases Chemical class 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
150000001728 carbonyl compounds Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
235000011613 Pinus brutia Nutrition 0.000 description 2
241000018646 Pinus brutia Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000003963 dichloro group Chemical group Cl* 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
229940102253 isopropanolamine Drugs 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
XMPCGZCCOXWBKR-UHFFFAOYSA-N 2,2,5-trimethyl-1,3-oxazolidine Chemical compound CC1CNC(C)(C)O1 XMPCGZCCOXWBKR-UHFFFAOYSA-N 0.000 description 1
FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 description 1
VSHIRTNKIXRXMI-UHFFFAOYSA-N 2,2-dimethyl-1,3-oxazolidine Chemical compound CC1(C)NCCO1 VSHIRTNKIXRXMI-UHFFFAOYSA-N 0.000 description 1
RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000000729 antidote Substances 0.000 description 1
229940075522 antidotes Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000009434 installation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000000463 material Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

JP51100109A 1975-08-28 1976-08-21 Ｎ−置換オキサゾリジン類の製法 Expired JPS5925788B2 (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US60847575A	1975-08-28	1975-08-28

Publications (2)

Publication Number	Publication Date
JPS5236662A JPS5236662A (en)	1977-03-22
JPS5925788B2 true JPS5925788B2 (ja)	1984-06-21

Family

ID=24436651

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP51100109A Expired JPS5925788B2 (ja)	1975-08-28	1976-08-21	Ｎ−置換オキサゾリジン類の製法

Country Status (18)

Country	Link
JP (1)	JPS5925788B2 (cs)
BE (1)	BE845577A (cs)
BG (1)	BG27551A3 (cs)
BR (1)	BR7605610A (cs)
CA (1)	CA1075701A (cs)
CH (1)	CH624946A5 (cs)
CS (1)	CS191316B2 (cs)
DD (1)	DD127680A5 (cs)
DE (1)	DE2637580C2 (cs)
FR (1)	FR2322141B1 (cs)
HU (1)	HU174379B (cs)
IL (1)	IL50192A (cs)
IT (1)	IT1066346B (cs)
NL (1)	NL181274C (cs)
PL (1)	PL100986B1 (cs)
RO (1)	RO69421A (cs)
SU (2)	SU814276A3 (cs)
YU (2)	YU40284B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5225570A (en) *	1987-08-13	1993-07-06	Monsanto Company	5-heterocyclic-substituted oxazolidine dihaloacetamides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1419330A1 (de) *	1962-06-09	1970-02-19	Hoechst Ag	Optische Aufhellungsmittel
BE757717A (cs) *	1969-10-21	1971-04-01

1976
- 1976-07-30 CA CA258,154A patent/CA1075701A/en not_active Expired
- 1976-08-03 IL IL50192A patent/IL50192A/xx unknown
- 1976-08-20 CH CH1064076A patent/CH624946A5/de not_active IP Right Cessation
- 1976-08-20 RO RO7687340A patent/RO69421A/ro unknown
- 1976-08-20 DE DE2637580A patent/DE2637580C2/de not_active Expired - Lifetime
- 1976-08-21 JP JP51100109A patent/JPS5925788B2/ja not_active Expired
- 1976-08-23 BR BR7605610A patent/BR7605610A/pt unknown
- 1976-08-25 PL PL1976191993A patent/PL100986B1/pl unknown
- 1976-08-25 YU YU2076/76A patent/YU40284B/xx unknown
- 1976-08-26 IT IT51031/76A patent/IT1066346B/it active
- 1976-08-26 BE BE7000872A patent/BE845577A/xx not_active IP Right Cessation
- 1976-08-26 DD DD194486A patent/DD127680A5/xx unknown
- 1976-08-26 BG BG034079A patent/BG27551A3/xx unknown
- 1976-08-27 CS CS765587A patent/CS191316B2/cs unknown
- 1976-08-27 NL NLAANVRAGE7609563,A patent/NL181274C/xx not_active IP Right Cessation
- 1976-08-27 HU HU76SA2966A patent/HU174379B/hu unknown
- 1976-08-27 FR FR7625928A patent/FR2322141B1/fr not_active Expired
- 1976-08-27 SU SU762391502A patent/SU814276A3/ru active
1978
- 1978-04-27 SU SU782607602A patent/SU727145A3/ru active
1982
- 1982-10-14 YU YU02318/82A patent/YU231882A/xx unknown

Also Published As

Publication number	Publication date
BR7605610A (pt)	1977-08-09
IL50192A0 (en)	1976-10-31
CH624946A5 (en)	1981-08-31
DE2637580C2 (de)	1990-08-02
NL7609563A (nl)	1977-03-02
CA1075701A (en)	1980-04-15
IL50192A (en)	1978-10-31
BE845577A (nl)	1977-02-28
RO69421A (ro)	1981-06-30
BG27551A3 (en)	1979-11-12
YU231882A (en)	1983-02-28
IT1066346B (it)	1985-03-04
SU727145A3 (ru)	1980-04-05
JPS5236662A (en)	1977-03-22
DD127680A5 (de)	1977-10-05
CS191316B2 (en)	1979-06-29
FR2322141A1 (fr)	1977-03-25
YU40284B (en)	1985-12-31
HU174379B (hu)	1979-12-28
PL100986B1 (pl)	1978-11-30
SU814276A3 (ru)	1981-03-15
FR2322141B1 (fr)	1980-04-04
YU207676A (en)	1983-02-28
NL181274C (nl)	1987-07-16
DE2637580A1 (de)	1977-03-17

Publication	Publication Date	Title
US3238224A (en)	1966-03-01	Production of 6, 8-dithiooctanoyl amides
JPS5925788B2 (ja)	1984-06-21	Ｎ−置換オキサゾリジン類の製法
US3238220A (en)	1966-03-01	3-hydroxy-benzisoxazoles and their production
US4851588A (en)	1989-07-25	Novel process for the preparation of bronopol
US3058992A (en)	1962-10-16	Intermediates for the preparation of
US4038284A (en)	1977-07-26	N-acylation of oxazolidines
HU193785B (en)	1987-11-30	Process for producing dihydropyridine derivatives
US2948725A (en)	1960-08-09	Flow sheet-process
JPS6115885A (ja)	1986-01-23	セフタジイムの製造
US2729678A (en)	1956-01-03	Phenyl halo-substituted salicylamide
US3244725A (en)	1966-04-05	4, 5-diacyl-3-hydroxy-3-pyrrolin-2-ones
US3145229A (en)	1964-08-18	Process for the production of nu-substituted-1-phenylcyclohexylamines
US1073380A (en)	1913-09-16	N-halogenalkyl-c c-dialkylbarbituric acids and preparation of the same.
US2568809A (en)	1951-09-25	Tetrahalomethylhexestrols and derivatives thereof
US2848494A (en)	1958-08-19	Process for converting optically active
JPH0348912B2 (cs)	1991-07-25
US4113948A (en)	1978-09-12	1-amino-1-phthalidyl alkanes and a method for producing same
US2517496A (en)	1950-08-01	Preparation of symmetrical monoaminodihydroxytoluene
US3108110A (en)	1963-10-22	1-[nu-lower alkyl-piperidyl-(4')]-3-phenyl-4-(parasubstituted benzyl)-pyrazolones
JPS61112056A (ja)	1986-05-30	イミダゾ−ル誘導体及びその製法
IL22743A (en)	1968-06-20	Compounds 1 ^ N -benzene-sulfonyl-2 ^ N-azabicyclo-octyl and nonyl urea and process for their production
JPS59152346A (ja)	1984-08-31	光学活性２−（６−メトキシ−２−ナフチル）プロピオン酸の製造法
JPH0285235A (ja)	1990-03-26	光学活性アミノアルコール類の製法
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