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

HRID 64855노트

반응식

HRID 64855 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-559ea23ee5204b5385c25514d08d3e8b
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04610981

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