Aniline → HCID 12832306、化合物

HRID 370767ノート

反応式

HRID 370767 の反応式
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[N:26]=[C:27]([SH:38])[NH:28][C:29]=2[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:21][CH:20]=1.[OH-].[Na+]>S(=O)(=O)(O)O.O.CN(C)C=O.C(Cl)Cl.[Cu]>[CH3:37][O:36][C:33]1[CH:34]=[CH:35][C:30]([C:29]2[N:28]=[C:27]([S:38][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[NH:26][C:25]=2[C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[CH:31][CH:32]=1

参加物

11

反応物 5

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 178489021HCID 178489021、化合物

生成物 1

HCID 12832306HCID 12832306、化合物収率 39.6%

試薬・触媒・溶媒 5

HCID 23978Copper触媒HCID 962Water溶媒4 回HCID 1118Sulfuric Acid溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

1.5 g of aniline is dissolved in 2.0 g of concentrated sulfuric acid and 30 ml of water and, after the addition of 10 g of ice, diazotized at 0° with a solution of 1.2 g of sodium nitrite in 10 ml of water. The diazonium salt solution is then neutralized with sodium acetate and introduced at 5° under thorough agitation into a solution of 5.02 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole in 200 ml of dimethylformamide containing 10 ml of water, 1.93 g of sodium hydroxide solution, as well as 1.15 g of powdered copper. The mixture is further stirred for 20 minutes, poured into 600 ml of water, the thus-precipitated oil is taken up in methylene chloride, the organic solution is washed with water, dried over sodium sulfate, and concentrated to dryness under vacuum. The residue is chromatographed on 200 g of silica gel. Elution with acetone/hexane 2:3 yields 2.47 g of 4,5-bis(4 -methoxy-phenyl)-2-(phenylthio)imidazole, mp 177°-179° after recrystallization from hexane/ethyl acetate.

後処理

  1. washthe organic solution is washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness under vacuum
  4. customThe residue is chromatographed on 200 g of silica gel
  5. washElution with acetone/hexane 2:3

出典と根拠

ORDレコード
ord-b60c345b5a7b4433b21f940a0797df0e
出典データセット
uspto-grants-1985_07
特許番号
US04528298

反応ノート

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