Isobutylamine → Benzenesulfonamide, N-(2-methylpropyl)-3-nitro-

Reaction equation

[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[N+:6]([C:9]1[CH:10]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7]>>[CH2:1]([NH:5][S:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=1)(=[O:16])=[O:17])[CH:2]([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 6558Isobutylamine

HCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 4591438Benzenesulfonamide, N-(2-methylpropyl)-3-nitro-Yield 78.8%

Procedure

The procedure described in Example 1A was performed using isobutylamine (0.396 g, 5.41 mmol) and 3-nitrobenzenesulfonyl chloride (1.0 g, 4.5 mmol) to give N-isobutyl-3-nitrobenzenesulfonamide (0.916 g, 78%). 1H NMR consistent with structure.

Sources & evidence

ORD record: ord-b692aad7b6db4e5591888863b72429b4
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127372

Reaction notes

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