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

HRID 1428786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428786
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b0101d33243a426498f1c37a848bdf2c
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937092B2

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