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Hydrochloric Acid → 4,5-Bis(4-methoxyphenyl)-2-(4-trifluoromethylphenylthio)imidazole

HRID 370803
ノート
印刷プレビュー

反応式

HRID 370803 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[H-].[Na+].[H][H].[F:27][C:28]([F:37])([F:36])[C:29]1[CH:35]=[CH:34][C:32](N)=[CH:31][CH:30]=1.N([O-])=O.[Na+].Cl>CN(C)C=O.[Cu]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][C:32]3[CH:34]=[CH:35][C:29]([C:28]([F:37])([F:36])[F:27])=[CH:30][CH:31]=3)[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 99644-(Trifluoromethyl)anilineHCID 24758Sodium hydrideHCID 23668193Sodium NitriteHCID 178418361HCID 178418361、化合物HCID 178489021HCID 178489021、化合物

生成物 1

HCID 12832305
4,5-Bis(4-methoxyphenyl)-2-(4-trifluoromethylphenylthio)imidazole
収率 37.1%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6228Dimethylformamide溶媒

実験手順

6.25 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole is dissolved in 150 ml of absolute dimethylformamide and combined with 0.60 g of sodium hydride (80% in oil). After the evolution of hydrogen has ceased, the solution is cooled to 0°, combined with a pinch of powdered copper, and then a diazonium salt solution, cooled to 0° and prepared from 3.26 g of 4-trifluoromethylaniline (99%), 1.38 g of sodium nitrite, as well as 10 ml of 6N hydrochloric acid, is added dropwise to the reaction mixture. The latter is agitated for 30 minutes at 0° and then allowed to warm up to room temperature. The solution is then concentrated under vacuum, the residue is distributed between water and ethyl acetate; the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is chromatographed on 500 g of aluminum oxide, neutral, activity stage II, with hexane/ethyl acetate 3:2 as the eluting agent. Elution yields 3.39 g of 4,5-bis(4-methoxyphenyl)-2-(4-trifluoromethylphenylthio)imidazole, mp 179°-181°.

後処理

  1. temperaturethe solution is cooled to 0°
  2. concentrationThe solution is then concentrated under vacuum
  3. dry with materialthe organic solution is dried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is chromatographed on 500 g of aluminum oxide
  6. washElution

出典と根拠

ORDレコード
ord-773c941b8abd487c8c901f089fe6b80d
出典データセット
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04528298

反応ノート

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