tert-Butanol → tert-butyl N-(2-fluoro-4-nitrobenzyl)sulfamoylcarbamate

HRID 1428786Notes

Reaction equation

HRID 1428786 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[CH2:23][NH2:24].C(N(CC)CC)C>ClCCl>[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[CH2:23][NH:24][S:2]([NH:5][C:6](=[O:7])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 45121148(2-Fluoro-4-nitrophenyl)methanamine

Product 1

HCID 86679394tert-butyl N-(2-fluoro-4-nitrobenzyl)sulfamoylcarbamateYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chlorosulfonyl isocyanate (0.1 mL) and t-butanol (0.12 mL) was mixed in dichloromethane. After 10 minutes, a solution of (2-fluoro-4-nitrophenyl)methanamine (200 mg, 1.176 mmol) in dichloromethane was added at 50° C. After stirring for 30 min the mixture was cooled to room temperature and triethylamine (0.11 mL) was added. After 3 h stirring at room temperature, the mixture was extracted with ethyl acetate and washed with brine. Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave tert-butyl N-(2-fluoro-4-nitrobenzyl)sulfamoylcarbamate (139 mg, 34%).

Workup

  1. stirringAfter 3 h stirring at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialDrying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography

Sources & evidence

ORD record
ord-b0101d33243a426498f1c37a848bdf2c
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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