Sodium benzenethiolate → 3-Nitro-6-phenylsulfanyl-imidazo[1,2-a]pyridine

HRID 839637노트

반응식

HRID 839637 반응식
[S-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Br[C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([N+:19]([O-:21])=[O:20])=[CH:17][N:18]=2)[CH:15]=1>CN1CCCC1=O>[N+:19]([C:16]1[N:14]2[CH:15]=[C:10]([S:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:11]=[CH:12][C:13]2=[N:18][CH:17]=1)([O-:21])=[O:20]

참가 물질

4

반응물 2

HCID 4110039Sodium benzenethiolateHCID 288758886-Bromo-3-nitroimidazo[1,2-a]pyridine

생성물 1

HCID 541282433-Nitro-6-phenylsulfanyl-imidazo[1,2-a]pyridine

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A solution of 1.61 g. (0.012 mole) of sodium thiophenoxide and 2.42 g. (0.01 mole) of 6-bromo-3-nitroimidazo [1,2-a] pyridine in 10 ml. N-methylpyrolidinone is heated at 150° C for 0.40 minutes under a nitrogen atmosphere. The cooled solution is poured onto 100 ml. of ice-water and the resultant suspension is extracted with ethyl acetate. The combined extracts are washed with saturated aqueous sodium chloride and dried over magnesium sulfate. Evaporation of the solvent to a small volume and dilution with N-hexane yields crystalline material. The solids are purified by chromatography on silica gel. Elution with methylene chloride yields pure 3-nitro 6-phenylthioimidazo [1,2-a] pyridine m.p. 108°-109° C.

후처리

  1. additionThe cooled solution is poured onto 100 ml
  2. extractionof ice-water and the resultant suspension is extracted with ethyl acetate
  3. washThe combined extracts are washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent to a small volume and dilution with N-hexane
  6. customyields crystalline material
  7. customThe solids are purified by chromatography on silica gel
  8. washElution with methylene chloride

출처 및 근거

ORD 기록
ord-cc9db0e1a7744171b906579d71098c49
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04096264

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