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

HRID 222159Notes

Reaction equation

HRID 222159 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]>C1C=CC=CC=1>[C:8]([O:12][C:6](=[O:7])[NH:5][S:2]([Cl:1])(=[O:4])=[O:3])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 15677406tert-butyl N-(chlorosulfonyl)carbamateYield 65.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of chlorosulfonyl isocyanate (3.20 mL, 36.0 mmol) in benzene (15.0 mL) in a water bath at rt was added tert-butyl alcohol (3.50 mL, 36.2 mmol) dropwise via syringe under an atmosphere of nitrogen. After 2 h, the mixture was diluted with hexanes (30.0 mL) and the resulting white precipitate was filtered and washed with hexanes (3×20 mL). The collected solid was dried in a vacuum desiccator under house vacuum for 10 min to afford the title compound as a white solid (5.08 g, 65%). The product was stored under nitrogen in a freezer. 1H NMR (300 MHz, CDCl3, δ): 8.44 (br s, 1H), 1.57 (s, 9H) ppm. LC/MS: Rt=0.939 min, ES+ 215 (AA standard). Reference: F. Hirayama et al., Biorg. Med. Chem., 2002, 10, 1509-1523.

Workup

  1. filtrationthe resulting white precipitate was filtered
  2. washwashed with hexanes (3×20 mL)
  3. customThe collected solid was dried in a vacuum desiccator under house vacuum for 10 min

Sources & evidence

ORD record
ord-c1c5b507d6ee415587c23ac1cfc4ebae
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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