Benzyl Alcohol → benzyl N-(chlorosulfonyl)carbamate

HRID 327658Notes

Reaction equation

HRID 327658 reaction equation
[Cl:1][S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([O:15][C:6]([NH:5][S:2]([Cl:1])(=[O:4])=[O:3])=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 14947136benzyl N-(chlorosulfonyl)carbamateYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 43.5 ml (0.5 mole) of chlorosulfonyl isocyanate in 400 ml of methylene chloride, stirred in an ice bath, was added 51.6 ml (0.5 mole) of benzyl alcohol over an one hr period. The reaction mixture was concentrated under reduced pressure and the solid residue was triturated in petroleum ether (bp range 35°-65° C.). The solid was collected by filtration, rinsed twice with petroleum ether and dried under vacuum to give 110 g (88% yield) of benzyloxycarbonylsulfamoyl chloride.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe solid residue was triturated in petroleum ether (bp range 35°-65° C.)
  3. filtrationThe solid was collected by filtration
  4. washrinsed twice with petroleum ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ddc7757684634dcca703b0b7c5f38454
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

Loading…