Triethylamine → N-(3-Bromo-propyl)-4-cyano-benzenesulfonamide

HRID 1992357Notes

Reaction equation

HRID 1992357 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].Br.[Br:14][CH2:15][CH2:16][CH2:17][NH2:18].C(N(CC)CC)C>ClCCl>[Br:14][CH2:15][CH2:16][CH2:17][NH:18][S:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 43133733N-(3-Bromo-propyl)-4-cyano-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Cyanobenzenesulfonyl chloride (5 g, 0.0248 mol) was added dropwise to a solution of 3-bromopropylamine hydrobromide (6.61 g, 0.0302 mol) and triethylamine (6.26 g, 0.062 mol) in dry dichloromethane (50 ml) at 0° C. and stirred at room temperature overnight under nitrogen atmosphere. The reaction was quenched with water and extracted with dichloromethane. The organic layer was washed with water, brine and dried over sodium sulfate.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-3af1aa919d5c4a828056269fa8c41bc5
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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