Catalyst system for manufacturing p-chlorophenyl-N-methyl carbam

Details Catalyst system for manufacturing p-chlorophenyl-N-methyl carbam Catalyst system for manufacturing p-chlorophenyl-N-methyl carbam

1981-10-19

1983-06-28

Moyer, Donald B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549452, 560 32, 560115, 560132, 560134, C07D30777, C07D31708, C07C12506

Patent

active

043907105

ABSTRACT:
Aromatic esters of carbamic acid derivatives, e.g., p-chlorophenyl-N-methyl carbamate, are prepared by reaction of the corresponding aromatic alcohol, e.g., p-chlorophenol, and monoisocyanate, e.g., methyl isocyanate, in the presence of a catalytic amount of a combination of a 4-aminopyridine catalyst, e.g., 4-dimethylaminopyridine, and pyridine or methyl substituted pyridines. The product is substantially pure, having less than 0.80 weight percent allophanate ester by-product, e.g., p-chlorophenyl-N,N'-dimethyl allophanate, and less than 0.50 weight percent unreacted aromatic alcohol, e.g., p-chlorophenol. The reaction is readily controlled and characterized by the substantial absence of reflux. The product can be retained in the liquid state at reaction temperature for extended periods of time without significantly increasing the level of allophanate ester by-product.

REFERENCES:
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patent: 2812247 (1957-11-01), Gysin et al.
patent: 3238036 (1966-03-01), Herrett
patent: 3341401 (1967-09-01), Kilsheimer et al.
patent: 3399048 (1968-08-01), Herrett
patent: 3470236 (1969-09-01), Hausweiler et al.
patent: 3597472 (1971-08-01), Heiss et al.
"4-Dialkylaminopyridines As Highly Active Acylation Catalysts," by Gerhard Hofle et al., Angew. Chem. Int. Ed. Engl. 17, 569-570 and 573-583 (1978).

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