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

HRID 1995200노트

반응식

HRID 1995200 반응식
[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

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 97092,4-DifluoroanilineHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178489021HCID 178489021, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23978Copper촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bb24c2bead1147038765fbc58255ce7d
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04402960

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