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

HRID 1947051Notes

Reaction equation

HRID 1947051 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8].CCCCCC>C1C=CC=CC=1>[C:11]([NH:10][S:7]([Cl:6])(=[O:9])=[O:8])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:12]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 8058HexaneHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 15677406tert-butyl N-(chlorosulfonyl)carbamateYield 91.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

t-Butanol (3 mL) was dissolved in dry benzene (10 mL) and cooled to 0° C. Chloro-sulfonyl isocyanate (CSI, 2 mL, 23.3 mmol) was added dropwise under N2, warmed up to RT, and stirred for 1 h. Hexane (40 mL) was added, cooled to 0° C. while stirring under N2, and the resulting white solid filtered off to provide N-Boc sulfamoyl chloride (4.55 g, 91.8% yield).

Workup

  1. temperaturewarmed up to RT
  2. temperaturecooled to 0° C.
  3. stirringwhile stirring under N2
  4. filtrationthe resulting white solid filtered off

Sources & evidence

ORD record
ord-a918101d69814f2ea1f05fe5a2905e8c
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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