Triethylamine → N-(3-bromopropyl)-3-cyano-benzenesulfonamide

HRID 1182090Notes

Reaction equation

HRID 1182090 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].CN(C1C=CC=CN=1)C.[C:16]([C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1)#[N:17].C(N(CC)CC)C>ClCCl>[Br:2][CH2:3][CH2:4][CH2:5][NH:6][S:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:16]#[N:17])[CH:19]=1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 787013-Bromopropylamine hydrobromideHCID 28013603-Cyanobenzene-1-sulfonyl chloride

Product 1

HCID 43133728N-(3-bromopropyl)-3-cyano-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A suspension of bromopropylamine hydrogen bromide (0.219 g, 1 mmol) in dichloromethane (2 ml) is treated with a solution of dimethylaminopyridine (0.004 g) in dichloromethane (0.5 ml) followed by a solution of 3-cyano-benzenesulfonyl chloride (0.2 g, 1.0 mmol) in dichloromethane (0.5 ml). Triethylamine (0.3 ml, 2.16 mmol) is added and the reaction mixture stirred at ambient temperature for 2 hours, then quenched with water and saturated aqueous NaHCO3, and extracted into dichloromethane. The organic phase is washed with aqueous 1M HCl solution and brine, dried over MgSO4 and evaporated to afford crude N-(3-bromopropyl)-3-cyano-benzenesulfonamide. (13C NMR, 100 MHz, CDCl3, 30.2, 32.6, 41.9, 114.3, 117.5, 130.7, 130.9, 131.1, 136.3, 142.1).

Workup

  1. customquenched with water and saturated aqueous NaHCO3
  2. extractionextracted into dichloromethane
  3. washThe organic phase is washed with aqueous 1M HCl solution and brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-73583611340749848866c9605af5837b
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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