JPS5980642A - 高立体障害性ｎ−オルガノアミドと炭酸エステルからｎ，ｎ−ビス（オルガノ）アミドを製造する方法 - Google Patents

高立体障害性ｎ−オルガノアミドと炭酸エステルからｎ，ｎ−ビス（オルガノ）アミドを製造する方法

Info

Publication number: JPS5980642A
Authority: JP; Japan
Prior art keywords: carbon atoms; alkyl; cycloalkyl; carbonate; organo
Prior art date: 1982-09-23
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.): Granted

Application number

JP16491583A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0114906B2 (fr

Inventor

ラルフ・ブリユ−スタ−・ソムプソン

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.)

PPG Industries Inc

Original Assignee

PPG Industries Inc

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.)

1982-09-23

Filing date

1983-09-06

Publication date

1984-05-10

1983-09-06 Application filed by PPG Industries Inc filed Critical PPG Industries Inc

1984-05-10 Publication of JPS5980642A publication Critical patent/JPS5980642A/ja

1989-03-14 Publication of JPH0114906B2 publication Critical patent/JPH0114906B2/ja

Status Granted legal-status Critical Current

Links

150000001408 amides Chemical class 0.000 title claims description 20
150000004651 carbonic acid esters Chemical class 0.000 title description 2
238000004519 manufacturing process Methods 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims description 46
125000000217 alkyl group Chemical group 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 31
238000000034 method Methods 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 22
125000000753 cycloalkyl group Chemical group 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
-1 organic carbonate esters Chemical class 0.000 claims description 14
125000000962 organic group Chemical group 0.000 claims description 14
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000005677 organic carbonates Chemical class 0.000 claims description 7
125000001246 bromo group Chemical group Br* 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 3
150000003138 primary alcohols Chemical class 0.000 claims description 3
239000007791 liquid phase Substances 0.000 claims description 2
239000002904 solvent Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000004423 acyloxy group Chemical group 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000000732 arylene group Chemical group 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
FWBMVXOCTXTBAD-UHFFFAOYSA-N butyl methyl carbonate Chemical compound CCCCOC(=O)OC FWBMVXOCTXTBAD-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 2
239000000203 mixture Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229960004793 sucrose Drugs 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
241000134884 Ericales Species 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
150000001412 amines Chemical group 0.000 description 1
125000005333 aroyloxy group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
ZGEPKHDCMGFQQP-UHFFFAOYSA-N benzyl methyl carbonate Chemical compound COC(=O)OCC1=CC=CC=C1 ZGEPKHDCMGFQQP-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
RVXBJNBDERKLJG-UHFFFAOYSA-N cyclohexyl methyl carbonate Chemical compound COC(=O)OC1CCCCC1 RVXBJNBDERKLJG-UHFFFAOYSA-N 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
KSCFJBIXMNOVSH-UHFFFAOYSA-N dyphylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC(O)CO)C=N2 KSCFJBIXMNOVSH-UHFFFAOYSA-N 0.000 description 1
238000005485 electric heating Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
229910052746 lanthanum Inorganic materials 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000009877 rendering Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
210000003625 skull Anatomy 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP16491583A 1982-09-23 1983-09-06 高立体障害性ｎ−オルガノアミドと炭酸エステルからｎ，ｎ−ビス（オルガノ）アミドを製造する方法 Granted JPS5980642A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US42222282A	1982-09-23	1982-09-23
US422222		1982-09-23

Publications (2)

Publication Number	Publication Date
JPS5980642A true JPS5980642A (ja)	1984-05-10
JPH0114906B2 JPH0114906B2 (fr)	1989-03-14

Family

ID=23673911

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16491583A Granted JPS5980642A (ja)	1982-09-23	1983-09-06	高立体障害性ｎ−オルガノアミドと炭酸エステルからｎ，ｎ−ビス（オルガノ）アミドを製造する方法

Country Status (4)

Country	Link
JP (1)	JPS5980642A (fr)
CH (1)	CH658452A5 (fr)
FR (1)	FR2533558B1 (fr)
GB (1)	GB2130202B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1282365B1 (it) *	1996-01-19	1998-03-20	Enichem Spa	Procedimento per l'alchilazione delle innidi

1983
- 1983-09-06 JP JP16491583A patent/JPS5980642A/ja active Granted
- 1983-09-22 FR FR8315093A patent/FR2533558B1/fr not_active Expired
- 1983-09-23 CH CH518883A patent/CH658452A5/fr not_active IP Right Cessation
- 1983-09-23 GB GB08325492A patent/GB2130202B/en not_active Expired

Also Published As

Publication number	Publication date
CH658452A5 (fr)	1986-11-14
GB2130202A (en)	1984-05-31
GB8325492D0 (en)	1983-10-26
FR2533558A1 (fr)	1984-03-30
GB2130202B (en)	1986-03-12
FR2533558B1 (fr)	1985-11-08
JPH0114906B2 (fr)	1989-03-14

Publication	Publication Date	Title
JPS5980642A (ja)	1984-05-10	高立体障害性ｎ−オルガノアミドと炭酸エステルからｎ，ｎ−ビス（オルガノ）アミドを製造する方法
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