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

HRID 2402264Notes

Reaction equation

HRID 2402264 reaction equation
[Cl:1][S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9]>ClCCl>[Cl:1][S:2]([NH:5][C:6](=[O:7])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanate2×

Product 1

HCID 15677406tert-butyl N-(chlorosulfonyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 5 L round bottom flask was charged with chlorosulfonyl isocyanate [Aldrich, product #142662] (149 mL, 1.72 mol) and dichloromethane (1.5 L) and cooled using an ice bath to 2° C. tert-Butanol (162 mL, 1.73 mol) in dichloromethane (200 mL) was added dropwise at a rate so that the temperature did not exceed 10° C. The resulting solution was stirred at room temperature for 30-60 min to provide tert-butyl [chlorosulfonyl]carbamate.

Workup

  1. temperaturecooled
  2. customto 2° C.
  3. additionwas added dropwise at a rate so that the temperature
  4. customdid not exceed 10° C

Sources & evidence

ORD record
ord-a477081943494b1eac7de3282158f3c7
Source dataset
uspto-grants-2014_08
Patent number
US08796319B2

Reaction notes

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