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

HRID 1732476ノート

反応式

HRID 1732476 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-57d780f4cbfa487a890dd11758ccca6c
出典データセット
uspto-grants-1980_12
特許番号
US04237300

反応ノート

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