Benzimidazole → 1-[(3,4-Dihydro-2H(1,3)-thiazino[3,2-a]benzimidazole-2-yl)methyl]-4-(3,4,5-trimethoxycinnamoyl)piperazine

HRID 1164399

반응식

HRID 1164399 반응식
[N:1]1([CH2:7][CH:8]2NCC=[CH:10][S:9]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][CH:15]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[CH:28]=[CH:29][C:30](Cl)=[O:31].[CH2:40](N(CC)CC)C>C(Cl)(Cl)Cl.O>[S:9]1[C:10]2=[N:14][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]2[CH2:15][CH2:40][CH:8]1[CH2:7][N:1]1[CH2:2][CH2:3][N:4]([C:30](=[O:31])[CH:29]=[CH:28][C:27]2[CH:26]=[C:25]([O:24][CH3:23])[C:35]([O:36][CH3:37])=[C:34]([O:38][CH3:39])[CH:33]=2)[CH2:5][CH2:6]1

참가 물질

7

반응물 4

HCID 5798BenzimidazoleHCID 8471TriethylamineHCID 1120942-Propenoyl chloride, 3-(3,4,5-trimethoxyphenyl)-, (2E)-HCID 1317129353,4-dihydro-2-piperazinomethyl-2H-(1,3)-thiazine

생성물 1

HCID 540543361-[(3,4-Dihydro-2H(1,3)-thiazino[3,2-a]benzimidazole-2-yl)methyl]-4-(3,4,5-trimethoxycinnamoyl)piperazine수율 69.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매2회

실험 절차

To 20 ml of chloroform was dissolved 1.0 g (3.5 m mole) of 3,4-dihydro-2-piperazinomethyl-2H-(1,3)-thiazine[3,2-a[benzimidazole, followed by the dropwise addition of 1 g of 3,4,5-trimethoxycinnamoyl chloride in 10 ml of chloroform under ice-cooled stirring conditions. After ten minutes, 0.5 ml of triethylamine was added. The mixture was stirred for 3 hours at room temperature. After the completion of the reaction, the reaction mixture was added with water and extracted with chloroform. The chloroform layer was washed with water and then dried over anhydrous magnesium sulfate. Chloroform was evaporated under reduced pressure and the residue was chromatographed on silica gel and eluted with chloroform to obtain 1.2 g (Yield: 69.4%) of the intended product, m.p. 211°-212° C.;

후처리

  1. temperaturecooled
  2. waitAfter ten minutes
  3. stirringThe mixture was stirred for 3 hours at room temperature
  4. customAfter the completion of the reaction
  5. extractionextracted with chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customChloroform was evaporated under reduced pressure
  9. customthe residue was chromatographed on silica gel
  10. washeluted with chloroform

출처 및 근거

ORD 기록
ord-b80d2e60805f4767962bc8e229809c0e
출처 데이터셋
uspto-grants-1983_01
특허 번호
US04369309

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