Dimethyl Sulfoxide → toluene-4-sulfonic acid 4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenyl ester

HRID 1514880노트

반응식

HRID 1514880 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[NH2:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=1)=[O:6].[CH3:20][C:21]1[CH:28]=[C:27]([O:29]CC(=O)N2CCCC2)[CH:26]=[C:25]([CH3:38])[C:22]=1[CH:23]=O.[OH2:39].C[S:41]([CH3:43])=[O:42]>>[CH3:15][C:10]1[CH:9]=[C:8]([NH:7][C:5]([C:4]2[CH:16]=[CH:17][C:18]3[N:19]=[C:23]([C:22]4[C:25]([CH3:38])=[CH:26][C:27]([O:29][S:41]([C:43]5[CH:17]=[CH:16][C:4]([CH3:5])=[CH:3][CH:2]=5)(=[O:39])=[O:42])=[CH:28][C:21]=4[CH3:20])[NH:1][C:2]=3[CH:3]=2)=[O:6])[CH:13]=[CH:12][C:11]=1[CH3:14]

참가 물질

5

반응물 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 66965643HCID 66965643, 화합물HCID 866512572,6-Dimethyl-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzaldehyde

생성물 1

HCID 86651258toluene-4-sulfonic acid 4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenyl ester

실험 절차

To a solution of 3,4-diamino-N-(3,4-dimethyl-phenyl)-benzamide (102 mg) in DMSO (2 mL) were added 2,6-dimethyl-4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzaldehyde (116 mg) and FeCl3 (1.2 mL in 0.02M THF solution). The mixture was stirred in open air at ambient temperature overnight. The mixture was then diluted by water and extracted with EtOAc. The extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=20:80 to 80:10) to give toluene-4-sulfonic acid 4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenyl ester: MS (m/z) 540 (M+1).

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexane=20:80 to 80:10)

출처 및 근거

ORD 기록
ord-2b8a05fa91534d4ea23c603c5e333622
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222248B2

반응 노트

불러오는 중…