Acetone → phenyl N-methoxy-N-(2-methylphenyl)carbamate

HRID 1602125Notes

Reaction equation

HRID 1602125 reaction equation
[C:1](=[O:10])([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:2].[C:11]([O-:14])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O.[CH3:24][C:25]([CH3:27])=O>>[CH3:11][O:14][N:2]([C:24]1[CH:6]=[CH:5][CH:4]=[CH:9][C:25]=1[CH3:27])[C:1](=[O:10])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 69322Phenyl carbamate

Product 1

HCID 15767250phenyl N-methoxy-N-(2-methylphenyl)carbamate

Procedure

A mixture of 2.0 g (8.2 mmol) of the phenyl carbamate from Example 4a, 2 g (15 mmol) of K2CO3 and 1.3 g (10 mmol) of dimethyl sulfate in 20 ml of acetone is stirred for 3 hours at room temperature. The reaction mixture is then filtered and evaporated down, and the residue is purified by column chromatography with mixtures of cyclohexane and ethyl acetate. There is obtained 1.5 g (5.8 mmol=71%) of the title compound as a colorless oil, which slowly crystallizes (mp=60° C.).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customevaporated down
  3. customthe residue is purified by column chromatography with mixtures of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-928948cae4624d00a098a13fedaa9b4d
Source dataset
uspto-grants-1999_11
Patent number
US05981532

Reaction notes

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