Methyl Carbamate → 1-(4'-Chlorobenzenesulfonyl)-3-methoxycarbonyl urea

HRID 2106913Notes

Reaction equation

HRID 2106913 reaction equation
[C:1](=[O:5])([O:3][CH3:4])[NH2:2].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]=[C:17]=[O:18])(=[O:15])=[O:14])=[CH:9][CH:8]=1>C1(C)C=CC=CC=1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([S:13]([NH:16][C:17]([NH:2][C:1]([O:3][CH3:4])=[O:5])=[O:18])(=[O:14])=[O:15])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 11722Methyl CarbamateHCID 1385874-Chlorobenzenesulfonyl isocyanate

Product 1

HCID 230496231-(4'-Chlorobenzenesulfonyl)-3-methoxycarbonyl ureaYield 95.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl carbamate (43.0 grams, 0.57 moles) was stirred in 500 milliliters of dry toluene. 4-chlorobenzenesulfonyl isocyanate (125 grams, 0.57 moles) was added dropwise. An exothermic reaction occurred. The reaction mixture was kept at 80° C. for 11/2hours. It was then cooled and the percipitate removed by filtration. The filtered material was washed with toluene and dried. There was obtained 159 grams of the title product, m.p. 174°-175° C.

Workup

  1. customAn exothermic reaction
  2. customwas kept at 80° C. for 11
  3. custom2hours
  4. temperatureIt was then cooled
  5. customthe percipitate removed by filtration
  6. washThe filtered material was washed with toluene
  7. customdried

Sources & evidence

ORD record
ord-53d32ac8edef4dfa8388ab1d59426af3
Source dataset
uspto-grants-1990_06
Patent number
US04931580

Reaction notes

Loading…