4-Bromobenzyl bromide → Ammonium Hydroxide

HRID 22550

반응식

HRID 22550 반응식
C[N:2](C)C([N:5]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][O:13][Si](C)(C)C)[N:7]=[CH:6]1)=[O:4].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>C(#N)C>[NH4+:2].[OH-:4].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:7]2[C:8]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:9][N:5]=[CH:6]2)=[CH:22][CH:21]=1

참가 물질

5

반응물 2

HCID 685274-Bromobenzyl bromideHCID 112772221-Dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole

생성물 2

HCID 14923Ammonium HydroxideHCID 224668773-[1-(4-Bromobenzyl)-1H-imidazol-5-yl]-1-propanol

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 11.2 g of 1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)-1H-imidazole and 12.49 g of p-bromobenzyl bromide in 110 ml of acetonitrile is refluxed for 24 h. The solution is cooled to 0° and ammonia gas is bubbled through the reaction mixture for 5 min. After reacting an additional 45 min at room temperature, the solvent is evaporated. The residue is taken up in 100 ml of 1N hydrochloric acid and extracted with 50 ml of ether. The aqueous phase is adjusted to pH 8 and extracted with ethyl acetate (5×50 ml). The organic extracts are washed with water, dried over sodium sulfate and evaporated. The resulting oil is chromatographed on 530 g of silica gel with ethyl acetate:methanol:saturated NH4OH (90:5:5) to yield the title compound a) as an oil; NMR: δ5.00 (s, 2H).

후처리

  1. temperatureThe solution is cooled to 0°
  2. customammonia gas is bubbled through the reaction mixture for 5 min
  3. customthe solvent is evaporated
  4. extractionextracted with 50 ml of ether
  5. extractionextracted with ethyl acetate (5×50 ml)
  6. washThe organic extracts are washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe resulting oil is chromatographed on 530 g of silica gel with ethyl acetate

출처 및 근거

ORD 기록
ord-68d3766580a044eb83b33e36ee4989e6
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428160

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