Aniline → HCID 12832306, 화합물

HRID 370767노트

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HRID 370767 반응식
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

참가 물질

11

반응물 5

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 178489021HCID 178489021, 화합물

생성물 1

HCID 12832306HCID 12832306, 화합물수율 39.6%

시약·촉매·용매 5

HCID 23978Copper촉매HCID 962Water용매4회HCID 1118Sulfuric Acid용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b60c345b5a7b4433b21f940a0797df0e
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04528298

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