4-(Bromomethyl)benzonitrile → 3-[1-(4-Cyanobenzyl)-1H-imidazol-5-yl]-1-propanol

HRID 477966

반응식

HRID 477966 반응식
CN(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.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1>C(#N)C.Cl>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:7]2[C:8]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:9][N:5]=[CH:6]2)=[CH:22][CH:23]=1)#[N:28]

참가 물질

5

반응물 2

HCID 869964-(Bromomethyl)benzonitrileHCID 112772221-Dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole

생성물 1

HCID 136882083-[1-(4-Cyanobenzyl)-1H-imidazol-5-yl]-1-propanol

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6342Acetonitrile용매

실험 절차

A solution of 97.0 g of 1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl) -1H-imidazole and 72.0 g of 1-bromomethyl-4-cyanobenzene in 500 ml of acetonitrile is refluxed for 10 h. The solution is cooled to 0° in an ice bath and ammonia gas is bubbled in for a few minutes. The mixture is then evaporated in vacuo to give a semisolid which is dissolved in 500 ml of 1N hydrochloric acid. The solution is allowed to stand at room temperature for 15 min and then is extracted with ether. The pH of the aqueous phase is adjusted to 9 with 50% sodium hydroxide solution and the mixture is then extracted with methylene chloride. The methylene chloride extracts are washed with water, dried over sodium sulfate and evaporated to give a semi-solid which is triturated with cold acetone to yield the title compound (b) as a white solid, m.p. 121°-123°.

후처리

  1. temperatureThe solution is cooled to 0° in an ice bath
  2. customammonia gas is bubbled in for a few minutes
  3. customThe mixture is then evaporated in vacuo
  4. customto give a semisolid which
  5. extractionis extracted with ether
  6. extractionthe mixture is then extracted with methylene chloride
  7. washThe methylene chloride extracts are washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customto give a semi-solid which
  11. customis triturated with cold acetone

출처 및 근거

ORD 기록
ord-1396dbdf933f402a95ceab74d731a70e
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04889861

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