Water → 4-acetyl-N-(tert-butyldimethylsiloxy)benzenesulfonamide

HRID 347352

Reaction equation

HRID 347352 reaction equation
[Si:1]([O:8][NH2:9])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)(=[O:19])[CH3:18].O>C1COCC1>[C:17]([C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])(=[O:28])=[O:27])=[CH:24][CH:25]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2664184-Acetylbenzenesulfonyl chlorideHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamine

Product 1

HCID 210825284-acetyl-N-(tert-butyldimethylsiloxy)benzenesulfonamideYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ex-33A: To a solution of O-(tert-butyldimethylsilyl)hydroxylamine (0.74 g, 5 mmol) and triethylamine (1.01 g, 10 mmol) in 25 ml THF, 4-acetylbenzenesulfonyl chloride(1.1 g, 5 mmol) was added at 0° C. The mixture was stirred overnight and then poured into H2O. The precipitate was filtered, dried, and recrystallized from EtOAc/Hexene to give 1.3 g (76.8%) of 4-acetyl-N-(tert-butyldimethylsiloxy)benzenesulfonamide as a white solid. 1H-NMR (300 MHz, CDCl3) δ 8.11 (d, J=9 Hz, 2H), 8.01 (d, J=9 Hz, 2H), 6.59 (b, 1H), 2.67 (s, 3H), 0.89 (s, 9H), 0.20 (s, 6H).

Workup

  1. filtrationThe precipitate was filtered
  2. customdried
  3. customrecrystallized from EtOAc/Hexene

Sources & evidence

ORD record
ord-8405d919c0c34009802b017a6c56ebd7
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Linked notes

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