Ethanol → HCID 12043498, compound

HRID 2296798Notes

Reaction equation

HRID 2296798 reaction equation
Br[CH:2]1[CH2:19][CH2:18][C:5]2=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:7][C:8]([S:9][CH2:10][CH2:11][CH3:12])=[C:4]2[C:3]1=O.[C:21]([NH2:29])(=[S:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)C>O>[C:22]1([C:21]2[S:28][C:2]3[CH2:19][CH2:18][C:5]4=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:7][C:8]([S:9][CH2:10][CH2:11][CH3:12])=[C:4]4[C:3]=3[N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 683563ThiobenzamideHCID 18388324HCID 18388324, compound

Product 1

HCID 12043498HCID 12043498, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 5-bromo-4,5,6,7-tetrahydro-4-oxo-3-propylthiobenzo[c]thiophene-1-carboxylate (9.43 g), thiobenzamide (6.86 g) and ethanol (190 ml) was refluxed under heating for 4 hours, after which it was poured over water (600 ml) and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:10, v/v) to yield ethyl 4,5-dihydro-2-phenyl-8-propylthiothieno[3,4-e]benzothiazole-6-carboxylate (3.63 g, 34.9%), which was then recrystallized from ethyl acetate-hexane. Yellow prisms. Melting point 125-126° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationafter which the solvent was distilled off
  7. washeluted with ethyl acetate-hexane (1:10

Sources & evidence

ORD record
ord-5dfad027f4a94ab39742535bc6119763
Source dataset
uspto-grants-2002_12
Patent number
US06489351B1

Reaction notes

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