Benzyl Alcohol → benzyl N-(chlorosulfonyl)carbamate

HRID 1613364Notes

Reaction equation

HRID 1613364 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-0b82cd3df8f143b49281b44ee049432a
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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