p-Bromobenzenesulfonyl chloride → 4-Bromo-N-[4-(1H-imidazol-1-yl)butyl]benzenesulfonamide

HRID 64855Notes

Reaction equation

HRID 64855 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH2:10])[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)(O)[O-].[Na+].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:10][CH2:9][CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 43794804-(1H-imidazol-1-yl)butan-1-amine

Product 1

HCID 136873094-Bromo-N-[4-(1H-imidazol-1-yl)butyl]benzenesulfonamideYield 30.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.39 g of 1H-imidazole-1-butanamine in 50 ml of dichloromethane at room temperature, covered with an excess of saturated sodium bicarbonate solution was added 2.55 g of 4-bromobenzenesulfonyl chloride. Stirring was continued for 22 hours, then the layers were separated and the organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethanol. The recrystallized material was dissolved in dichloromethane containing 5% ethanol. The solution was passed through a silica gel column. The column was washed twice with 200 ml portions of ethyl acetate, then three times with 200 ml portions of 10% ethanol/ethyl acetate. The 10% ethanol/ethyl acetate cuts were combined and evaporated in vacuo, the residue was dried in vacuo at 50° C. and gave 1.09 g of the compound of the Example as colorless crystals, mp 158°-159° C.

Workup

  1. customat room temperature
  2. customthe layers were separated
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from ethanol
  6. dissolutionThe recrystallized material was dissolved in dichloromethane containing 5% ethanol
  7. washThe column was washed twice with 200 ml portions of ethyl acetate
  8. customevaporated in vacuo
  9. customthe residue was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-559ea23ee5204b5385c25514d08d3e8b
Source dataset
uspto-grants-1986_09
Patent number
US04610981

Reaction notes

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