2,6-Dimethoxybenzoyl chloride → 2-isocyanato-1,3-dimethoxybenzene

HRID 2071506Notes

Reaction equation

HRID 2071506 reaction equation
COC1C=CC=C(OC)C=1C(Cl)=O.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:17]=1[N:24]=[C:25]=[O:26].[CH3:27][N:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[NH:33]>C1C=CC=CC=1>[CH3:27][N:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[NH:33].[CH3:23][O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH3:14])[C:17]=1[N:24]=[C:25]=[O:26].[CH3:27][N:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[N:33][C:25]([NH:24][C:17]1[C:16]([O:15][CH3:14])=[CH:21][CH:20]=[CH:19][C:18]=1[O:22][CH3:23])=[O:26]

Participants

7

Reactant 3

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 27361992-isocyanato-1,3-dimethoxybenzeneHCID 124489661-Methyl-2-pyrrolidinimine

Product 3

HCID 27361992-isocyanato-1,3-dimethoxybenzeneHCID 3039367HCID 3039367, compoundHCID 124489661-Methyl-2-pyrrolidinimine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A solution of 1-methyl-2-iminopyrrolidine in benzene is prepared from 10.73 g. (0.08 mole) of the hydrochloride salt in the usual manner. 2,6-Dimethoxyphenylisocyanate is prepared in 81% yield (crude) from 2,6-dimethoxybenzoyl chloride by the method of K. Inukai and Y. Maki, Kogyo Kagaku Zasshi, 67, (5) 807-9 (1964). A benzene solution of 13.45 g. (0.075 mole) of the 2,6-dimethoxyphenylisocyanate is added to the benzene solution of 1-methyl-2-iminopyrrolidine and the reaction mixture is stirred for 1.5 hours at room temperature. A white precipitate, which forms, is filtered off and discarded. The filtrate is reduced to dryness under reduced pressure to give a clear, viscous oil that crystallizes on cooling. Recrystallizations from ethyl acetate-ether and ethyl acetate gives 1-(1-methyl-2-pyrrolidylidene)-3-(2,6-dimethoxyphenyl)urea as white crystals, m.p. = 114°-117° C.

Workup

  1. filtrationis filtered off
  2. customto give a clear, viscous oil that
  3. customcrystallizes
  4. temperatureon cooling
  5. customRecrystallizations from ethyl acetate-ether and ethyl acetate

Sources & evidence

ORD record
ord-c3b3be1c7d534e41b5657acb2497c1bc
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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