IL34090A - Process for the preparation of N-alkyl for cuts with at least 01 members in the ring - Google Patents

Process for the preparation of N-alkyl for cuts with at least 01 members in the ring

Info

Publication number: IL34090A
Authority: IL; Israel
Prior art keywords: ether; sulphate; process according; lactam; give
Prior art date: 1969-03-18

Application number

IL34090A

Other languages

English (en)

Hebrew (he)

Other versions

IL34090A0 (en

Original Assignee

Inventa Ag

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.)

1969-03-18

Filing date

1970-03-16

Publication date

1972-11-28

1970-03-16 Application filed by Inventa Ag filed Critical Inventa Ag

1970-05-21 Publication of IL34090A0 publication Critical patent/IL34090A0/xx

1972-11-28 Publication of IL34090A publication Critical patent/IL34090A/en

Links

238000000034 method Methods 0.000 title claims description 31
238000002360 preparation method Methods 0.000 title claims description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 57
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 23
229910021653 sulphate ion Inorganic materials 0.000 claims description 23
150000003951 lactams Chemical class 0.000 claims description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 8
238000004821 distillation Methods 0.000 claims description 7
238000006317 isomerization reaction Methods 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
238000001035 drying Methods 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 8
150000002170 ethers Chemical class 0.000 description 7
238000003756 stirring Methods 0.000 description 7
230000029936 alkylation Effects 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
238000009835 boiling Methods 0.000 description 6
238000007792 addition Methods 0.000 description 5
239000003513 alkali Substances 0.000 description 5
-1 caprolactim ethers Chemical class 0.000 description 5
238000001816 cooling Methods 0.000 description 5
JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000004952 Polyamide Substances 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000243 solution Substances 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000820057 Ithone Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D227/00—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
- C07D227/02—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D227/06—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D227/08—Oxygen atoms
- C07D227/087—One doubly-bound oxygen atom in position 2, e.g. lactams

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Cephalosporin Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL34090A 1969-03-18 1970-03-16 Process for the preparation of N-alkyl for cuts with at least 01 members in the ring IL34090A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH402969A CH507948A (de)	1969-03-18	1969-03-18	Verfahren zur Herstellung von mindestens 10 Ringglieder aufweisenden N-Alkyl-lactamen

Publications (2)

Publication Number	Publication Date
IL34090A0 IL34090A0 (en)	1970-05-21
IL34090A true IL34090A (en)	1972-11-28

Family

ID=4268468

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL34090A IL34090A (en)	1969-03-18	1970-03-16	Process for the preparation of N-alkyl for cuts with at least 01 members in the ring

Country Status (13)

Country	Link
US (1)	US3711465A (es)
JP (1)	JPS4839947B1 (es)
AT (1)	AT293351B (es)
BE (1)	BE747428A (es)
BR (1)	BR7017527D0 (es)
CH (1)	CH507948A (es)
DE (1)	DE2012434C3 (es)
ES (1)	ES377568A1 (es)
FR (1)	FR2039648A5 (es)
GB (1)	GB1278844A (es)
IE (1)	IE33754B1 (es)
IL (1)	IL34090A (es)
NL (1)	NL7003711A (es)

1969
- 1969-03-18 CH CH402969A patent/CH507948A/de not_active IP Right Cessation
1970
- 1970-03-16 IL IL34090A patent/IL34090A/en unknown
- 1970-03-16 ES ES377568A patent/ES377568A1/es not_active Expired
- 1970-03-16 AT AT240970A patent/AT293351B/de not_active IP Right Cessation
- 1970-03-16 DE DE2012434A patent/DE2012434C3/de not_active Expired
- 1970-03-16 BE BE747428D patent/BE747428A/xx unknown
- 1970-03-16 NL NL7003711A patent/NL7003711A/xx unknown
- 1970-03-17 FR FR7009554A patent/FR2039648A5/fr not_active Expired
- 1970-03-17 GB GB02848/70A patent/GB1278844A/en not_active Expired
- 1970-03-17 BR BR217527/70A patent/BR7017527D0/pt unknown
- 1970-03-17 US US00020406A patent/US3711465A/en not_active Expired - Lifetime
- 1970-03-18 IE IE346/70A patent/IE33754B1/xx unknown
- 1970-03-18 JP JP45022993A patent/JPS4839947B1/ja active Pending

Also Published As

Publication number	Publication date
BE747428A (fr)	1970-08-31
US3711465A (en)	1973-01-16
DE2012434A1 (de)	1970-10-01
ES377568A1 (es)	1972-07-01
DE2012434B2 (de)	1973-05-17
BR7017527D0 (pt)	1973-01-09
IL34090A0 (en)	1970-05-21
JPS4839947B1 (es)	1973-11-28
CH507948A (de)	1971-05-31
FR2039648A5 (es)	1971-01-15
NL7003711A (es)	1970-09-22
IE33754B1 (en)	1974-10-16
IE33754L (en)	1970-09-18
AT293351B (de)	1971-10-11
DE2012434C3 (de)	1973-12-06
GB1278844A (en)	1972-06-21

Publication	Publication Date	Title
HU207284B (en)	1993-03-29	Process for producing 1-amino-methyl-1-cyclohexane-acetic acid
US4864026A (en)	1989-09-05	Method of manufacturing N-alkyl-N'-methyl-alkyleneureas, particularly N,N'-d
CA2034640A1 (en)	1991-08-07	Process for the preparation of 3-cyano-3, 5, 5-trimethylcyclohexanone
US3435074A (en)	1969-03-25	Process for producing nitrodiarylamines
EP0456838B1 (en)	1995-11-02	Process for producing glycine
IL34090A (en)	1972-11-28	Process for the preparation of N-alkyl for cuts with at least 01 members in the ring
US4020104A (en)	1977-04-26	Process for isomerizing cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer
US4968839A (en)	1990-11-06	Synthetic process for the preparation of N,N dimethyl glycine (DMG)
US2333696A (en)	1943-11-09	Chemical process
US6281394B1 (en)	2001-08-28	Method for producing vicinal diols or polyols
US4960938A (en)	1990-10-02	Preparing 2-chlorobenzylamine from 2-chlorobenzylchloride via 2-chlorobenzylphthalimide
US4058563A (en)	1977-11-15	Novel schiff bases
EP0055630B1 (en)	1985-12-18	Method for the preparation of fluorophthalamic compounds
US4590295A (en)	1986-05-20	Process for the manufacture of p-hydroxyphenyl-acetic acid
US4152530A (en)	1979-05-01	Process for preparing allylic alcohols from allylic halides
AU1766792A (en)	1992-11-02	Process for conducting chemical reactions with formaldehyde
JPH0273033A (ja)	1990-03-13	４，４―ジメチル―１―（ｐ―クロロフエニル）ペンタン―３―オンの製造方法
FR2581060A1 (fr)	1986-10-31	Procede industriel d'obtention du midalcipran
US2425283A (en)	1947-08-05	Preparation of allylglycine
US4774358A (en)	1988-09-27	Cyclopropylamines containing trifluoromethyl groups
Ishikawa et al.	1974	REACTIONS OF PERFLUORO-2-METHYLPENTENE-2 WITH AROMATIC NUCLEOPHILES
US6037503A (en)	2000-03-14	Process for the preparation of para-fluorophenol
US2673219A (en)	1954-03-23	Manufacture of pimelic acid
US4614803A (en)	1986-09-30	Process for the preparation of dry alkali metal salts of 1,8-naphthalimide
SU530025A1 (ru)	1976-09-30	Способ получени азиридинов