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

HRID 1995200ノート

反応式

HRID 1995200 の反応式
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1N.N([O-])=O.[Na+].Cl.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]([SH:36])[NH:26][C:27]=2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:19][CH:18]=1.[OH-].[Na+]>CN(C)C=O.[Cu]>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([C:27]2[N:26]=[C:25]([S:36][C:3]3[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=3[F:1])[NH:24][C:23]=2[C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[CH:29][CH:30]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 97092,4-DifluoroanilineHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178489021HCID 178489021、化合物

生成物 1

HCID 128323094,5-Bis(4-methoxyphenyl)-2-(2,4-difluorophenylthio)imidazole収率 36.8%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6228Dimethylformamide溶媒

実験手順

At 0° a diazonium salt solution prepared from 2.58 g of 2,4-difluoroaniline, 1.58 g of sodium nitrite, and 10 ml of 6 N hydrochloric acid is added dropwise to a solution of 6.25 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole in a mixture of 240 ml of dimethylformamide, 10 ml of 2 N sodium hydroxide solution, and 1.45 g of powdered copper. The solution becomes reddish brown under nitrogen evolution. The mixture is stirred for another 3 hours, the solution is concentrated under vacuum, and 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 subjected to column chromatography on 500 g of neutral aluminum oxide (activity stage II). Elution with acetone/hexane 2:3 yields 3.12 g of 4,5-bis(4-methoxyphenyl)-2-(2,4-difluorophenylthio)imidazole, having a melting point of 174°-176° after crystallization from hexane/ether and a melting point of 186°-188° after another crystallization from ethanol/ether.

後処理

  1. concentrationthe solution is concentrated under vacuum
  2. dry with materialThe organic solution is dried over sodium sulfate
  3. concentrationconcentrated to dryness under vacuum
  4. washElution with acetone/hexane 2:3

出典と根拠

ORDレコード
ord-bb24c2bead1147038765fbc58255ce7d
出典データセット
uspto-grants-1983_09
特許番号
US04402960

反応ノート

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