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

HRID 1778472Notes

Reaction equation

HRID 1778472 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]>C(Cl)Cl>[C:8]([O:12][C:6]([NH:5][S:2]([Cl:1])(=[O:4])=[O:3])=[O:7])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 15677406tert-butyl N-(chlorosulfonyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of chlorosulfonyl isocyanate (0.087 mL, 1 mmol) in CH2Cl2 (20 mL) was added tert-butanol (0.096 mL, 1 mmol) in ice-bath. The mixture was stirred at room temperature for 2 hours. A solution of N-tert-butoxycarbonylsulfamoyl chloride in CH2Cl2 (−0.05 M) was obtained, which was used for next step without further purification.

Sources & evidence

ORD record
ord-596d98fc7e9745689d2547ae30a89069
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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