Triethylamine → N-(2-bromoethyl)-4-cyanobenzenesulfonamide

HRID 1992343Notes

Reaction equation

HRID 1992343 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.[C:13]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)#[N:14]>ClCCl>[Br:2][CH2:3][CH2:4][NH:5][S:21]([C:18]1[CH:17]=[CH:16][C:15]([C:13]#[N:14])=[CH:20][CH:19]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 43133684N-(2-bromoethyl)-4-cyanobenzenesulfonamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To an ice cooled solution of 2-bromoethylamine hydrogenbromide (12.2 g, 0.0595 mol) in dry dichloromethane (100 mL) was added triethylamine and the mixture stirred for 15 min. 4-Cyanobenzenesulfonyl chloride (10 g, 0.0486 mol) in dichloromethane was added, dropwise. Stirring was continued at RT for 1 h. The reaction mixture was diluted with dichloromethane, washed with water, followed by brine, then dried over sodium sulfate. Solvents were evaporated and the residue crystallized from petroleum ether to give 12.5 g of the sub-title compound as a pale yellow solid.

Workup

  1. stirringStirring
  2. waitwas continued at RT for 1 h
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customSolvents were evaporated
  6. customthe residue crystallized from petroleum ether

Sources & evidence

ORD record
ord-d9eb4c9c94f74ab0a127637229421b54
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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