Benzene → 4-(2-chlorophenyl)-6,8-dimethyl-3-(3-methyl-4H-1,4-benzothiazin-2-carbonyl) aminoquinoline

HRID 259861

반응식

HRID 259861 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[CH:9][C:8]([CH3:19])=[CH:7][C:6]=2[CH3:20].C1C=CC=CC=1.[CH2:27]=[C:28]1[O:32][C:30](=O)[CH2:29]1.[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[SH:40]>C(N(CC)CC)C.O.CS(C)=O>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[C:10]2[C:5](=[C:6]([CH3:20])[CH:7]=[C:8]([CH3:19])[CH:9]=2)[N:4]=[CH:3][C:2]=1[NH:1][C:30]([C:29]1[S:40][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[NH:33][C:28]=1[CH3:27])=[O:32]

참가 물질

8

반응물 4

HCID 241BenzeneHCID 87132-AminothiophenolHCID 12661DiketeneHCID 104465363-Amino-4-(2-chlorophenyl)-6,8-dimethylquinoline

생성물 1

HCID 231701124-(2-chlorophenyl)-6,8-dimethyl-3-(3-methyl-4H-1,4-benzothiazin-2-carbonyl) aminoquinoline수율 26%

시약·촉매·용매 3

HCID 8471Triethylamine촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

A mixture of 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (1.0 g), triethylamine (2 drops) and benzene (5 ml) was heated to 70° C., and diketene (0.25 ml) was dropwise added thereto. The mixture was further heated at 70° C. for 30 minutes, and then, dimethylsulfoxide (15 ml) and 2-aminothiophenol (0.4 g) were added thereto. The resultant mixture was heated at 130° C. for an hour, diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with a solution of salt and dried (MgSO4). The solvent was removed and the residue was purified by a silica gel column chromatography with hexane-ethyl acetate (3:1,V/V), and then crystallized from ethyl acetate-ethyl ether to give 4-(2-chlorophenyl)-6,8-dimethyl-3-(3-methyl-4H-1,4-benzothiazin-2-ylcarbonyl) aminoquinoline (0.39 g, 26%) as yellowish prisms.

후처리

  1. temperatureThe mixture was further heated at 70° C. for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a solution of salt
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed
  6. customthe residue was purified by a silica gel column chromatography with hexane-ethyl acetate (3:1,V/V)
  7. customcrystallized from ethyl acetate-ethyl ether

출처 및 근거

ORD 기록
ord-47bfbe8bf51245bd94ad44f64906fae9
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05523407

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