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

HRID 1164399Notes

Reaction equation

HRID 1164399 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

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.;

Workup

  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

Sources & evidence

ORD record
ord-b80d2e60805f4767962bc8e229809c0e
Source dataset
uspto-grants-1983_01
Patent number
US04369309

Reaction notes

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