tert-Butanol → HCID 86679392, compound

HRID 1428776Notes

Reaction equation

HRID 1428776 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].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=1)([O-:15])=[O:14].C(N(CC)CC)C>ClCCl>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([CH2:22][NH:23][S:2]([NH:5][C:6](=[O:7])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:4])=[O:3])=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 291474-NitrobenzylamineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 86679392HCID 86679392, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chlorosulfonyl isocyanate (0.063 mL) and t-butanol (0.07 mL) were mixed in dichloromethane. After 10 min a solution of (4-nitrophenyl)methanamine (100 mg, 0.657 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. The mixture was stirred for 3 h, 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-(4-nitrobenzyl)sulfamoylcarbamate (112 mg, 51%).

Workup

  1. stirringThe mixture was stirred for 3 h
  2. extractionextracted 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-4f92f6d59a6f44fda26d17480c287c68
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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