2-Butanamine, 2-methyl- → 2-bromo-N-(1,1-dimethylpropyl)benzenesulfonamide

HRID 1296303Notes

Reaction equation

HRID 1296303 reaction equation
[CH3:1][C:2]([NH2:6])([CH2:4][CH3:5])[CH3:3].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14](Cl)(=[O:16])=[O:15]>ClCCl>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH:6][C:2]([CH3:3])([CH3:1])[CH2:4][CH3:5])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 689862-Butanamine, 2-methyl-HCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 48250202-bromo-N-(1,1-dimethylpropyl)benzenesulfonamideYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-methyl-2-butanamine (11.4 mL, 97.8 mmol) in dichloromethane (100 mL) was added, dropwise over a 10 min period, a solution of 2-bromobenzenesulfonyl chloride (10.0 g, 39.1 mmol) in dichloromethane (ca. 50 mL). After stirring for 15 h the reaction was concentrated in vacuo. The residue was crystallized from methyl t-butyl ether to provide 10.5 g (87%) of 2-bromo-N-(1,1-dimethylpropyl)benzenesulfonamide in two crops: LCMS (neg. ion spectrum) m/z 304/306.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was crystallized from methyl t-butyl ether

Sources & evidence

ORD record
ord-475cc827c719425fb9d2bf1909b9fd89
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

Loading…