Dimethyl Sulfate → phenyl N-methoxy-N-(2-methylphenyl)carbamate

HRID 362472Notes

Reaction equation

HRID 362472 reaction equation
O[N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])C(=O)[O-].[C:13]([O-:16])([O-])=[O:14].[K+].[K+].S([O:24][CH3:25])(OC)(=O)=O>C(Cl)Cl>[CH3:25][O:24][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])[C:13](=[O:14])[O:16][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178424385HCID 178424385, compound

Product 1

HCID 15767250phenyl N-methoxy-N-(2-methylphenyl)carbamateYield 157.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 407 g (1.6 mol) of N-hydroxy-N-(2-methylphenyl)carbamate (Example 2a) and 277 g (2.0 mol) of K2CO3 in 700 ml of CH2Cl2 is treated dropwise with 211 g (1.67 mol) of dimethyl sulfate. The reaction mixture warms to about 40° C. during the course of this. The reaction mixture is stirred overnight at room temperature and then filtered through kieselguhr. The filtrate is washed with NH3 soln. and water, dried over MgSO4 and concentrated. The residue crystallizes and is stirred with hexane. 324 g (75%) of the title compound are obtained as colorless solid.

Workup

  1. customwarms to about 40° C. during the course
  2. filtrationfiltered through kieselguhr
  3. washThe filtrate is washed with NH3 soln
  4. dry with materialand water, dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue crystallizes
  7. stirringis stirred with hexane

Sources & evidence

ORD record
ord-bb82d25eddf34153bc5565c3fe82b8d6
Source dataset
uspto-grants-1999_02
Patent number
US05869517

Reaction notes

Loading…