Ethyl chloroformate → Carbamate

HRID 1277841Notes

Reaction equation

HRID 1277841 reaction equation
[CH2:1]([S:3][C:4]1[CH:5]=[C:6]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:7]=[C:8]([S:10][CH2:11][CH3:12])[CH:9]=1)[CH3:2].Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>N1C=CC=CC=1>[CH2:11]([S:10][C:8]1[CH:7]=[C:6]([S:13]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:24](=[O:25])[O:26][CH2:27][CH3:28])=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH:5]=[C:4]([S:3][CH2:1][CH3:2])[CH:9]=1)[CH3:12].[C:24](=[O:25])([O-:26])[NH2:22]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 23451836HCID 23451836, compound

Product 2

HCID 276CarbamateHCID 53802442HCID 53802442, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

4-[[3,5-Bis(ethylthio)phenyl]sulfonyl]benzenamine (0.1 mole) and pyridine (50 ml) are charged into a glass reaction vessel fitted with a mechanical stirrer and thermometer and are cooled to about 5° C. Ethyl chloroformate (0.125 mole) is added, with stirring, at about 5° C. Stirring is continued for a period of about 30 minutes at about 5° C., then for an additional 16 hours at room temperature. The mixture is then washed with 2 portions of water (50 ml), dried and the solvent is then removed to yield the desired product ethyl [4-[3,5-bis(ethylthio)phenyl]sulfonyl]phenyl]carbamate.

Workup

  1. customfitted with a mechanical stirrer
  2. stirringStirring
  3. waitfor an additional 16 hours at room temperature
  4. washThe mixture is then washed with 2 portions of water (50 ml)
  5. customdried
  6. customthe solvent is then removed

Sources & evidence

ORD record
ord-e73694a04bfd41c5a25440dc4c84b760
Source dataset
uspto-grants-1981_07
Patent number
US04279637

Reaction notes

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