tert-Butanol → tert-butyl N-(chlorosulfonyl)carbamate

HRID 708441Notes

Reaction equation

HRID 708441 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[S:6]([Cl:12])([N:9]=[C:10]=[O:11])(=[O:8])=[O:7]>C1C=CC=CC=1>[Cl:12][S:6]([NH:9][C:10](=[O:11])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 15677406tert-butyl N-(chlorosulfonyl)carbamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of tert-butanol (3.2 g, 36.9 mmol) in benzene (13 mL) was added sulfurisocyanatidoyl chloride (3.5 mL, 36.6 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with hexane. The mixture was cooled in an ice-bath, resulted in white solid precipitation. The solid was filtered, washed with hexane, dried and used in the next step immediately (3.2 g, 41%).

Workup

  1. customthe reaction mixture was quenched with hexane
  2. temperatureThe mixture was cooled in an ice-bath
  3. customresulted in white solid precipitation
  4. filtrationThe solid was filtered
  5. washwashed with hexane
  6. customdried

Sources & evidence

ORD record
ord-6309e37dfa354127871cbe60bcad3ccc
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

Loading…