GB1022641A - A process for the preparation of dicarbamates with non-identical carbamate groups from diols - Google Patents

A process for the preparation of dicarbamates with non-identical carbamate groups from diols

Info

Publication number
GB1022641A
GB1022641A GB761862A GB761862A GB1022641A GB 1022641 A GB1022641 A GB 1022641A GB 761862 A GB761862 A GB 761862A GB 761862 A GB761862 A GB 761862A GB 1022641 A GB1022641 A GB 1022641A
Authority
GB
Grant status
Application
Patent type
Prior art keywords
group
mols
amine
mol
reaction
Prior art date
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
GB761862A
Inventor
Francois Molnar
Albert Lachavanne
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.)
ORGAMOL SA
Original Assignee
ORGAMOL SA
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.)
Filing date
Publication date

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00Preparation of esters of carbonic or haloformic acids
    • C07C68/02Preparation of esters of carbonic or haloformic acids from phosgene or haloformates

Abstract

Non-symmetric dicarbamates of the formula <FORM:1022641/C2/1> where R1 is a C1- 6 alkyl group and R2 and R3 are different and may be hydrogen or a C1- 6 alkyl group, are made by reacting (a) one mol. of a diol <FORM:1022641/C2/2> with 2 mols. phosgene in the presence of 2 mols. of an acid acceptor to form the dichlorocarbonate, (b) blocking one of the chlorocarbonate groups by reacting the dichlorocarbonate with one mol. of a tertiary amine, (c) converting the unblocked chlorocarbonate group into a carbamate group by reaction with two mols. of ammonia or a primary amine NH2R, at a temperature not exceeding 20 DEG C., and (d) converting the blocked carbonate group into a carbamate group different from that of step (c) by reaction with 2 mols. of ammonia or a primary amine, NH2R3, under more active conditions than those of step (c). In steps (c) and (d) the second mol. of ammonia or amine acts as an acidacceptor. Step (d) is suitably effected at super-atmospheric pressures and/or temperatures up to 50 DEG C. The reaction may be effected in a solvent, e.g. halogenated aliphatic hydrocarbons or aromatic hydrocarbons. Examples relate to (1) and (3) N-isopropyl-2-methyl-2-n-propyl-1,3-propanediol dicarbamate, and (2) N - n - butyl - 2 - methyl - 2 - n - propyl - 1,3-propanediol dicarbamate.
GB761862A 1962-02-27 1962-02-27 A process for the preparation of dicarbamates with non-identical carbamate groups from diols Expired GB1022641A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB761862A GB1022641A (en) 1962-02-27 1962-02-27 A process for the preparation of dicarbamates with non-identical carbamate groups from diols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB761862A GB1022641A (en) 1962-02-27 1962-02-27 A process for the preparation of dicarbamates with non-identical carbamate groups from diols

Publications (1)

Publication Number Publication Date
GB1022641A true true GB1022641A (en) 1966-03-16

Family

ID=9836571

Family Applications (1)

Application Number Title Priority Date Filing Date
GB761862A Expired GB1022641A (en) 1962-02-27 1962-02-27 A process for the preparation of dicarbamates with non-identical carbamate groups from diols

Country Status (1)

Country Link
GB (1) GB1022641A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0823419A2 (en) * 1996-08-09 1998-02-11 Takeda Chemical Industries, Ltd. Dimethylpropanediol compounds
WO2006072966A1 (en) * 2005-01-03 2006-07-13 Shasun Chemicals And Drugs Limited High-bulk density carisoprodol suitable for direct compression

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0823419A2 (en) * 1996-08-09 1998-02-11 Takeda Chemical Industries, Ltd. Dimethylpropanediol compounds
EP0823419A3 (en) * 1996-08-09 2000-08-16 Takeda Chemical Industries, Ltd. Dimethylpropanediol compounds
WO2006072966A1 (en) * 2005-01-03 2006-07-13 Shasun Chemicals And Drugs Limited High-bulk density carisoprodol suitable for direct compression

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