Ethanol → 161190-38-1

HRID 1736406Notes

Reaction equation

HRID 1736406 reaction equation
C(O)C.[CH3:4][C:5]1[CH:10]=[C:9](Br)[CH:8]=[CH:7][C:6]=1[N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[S:17]([CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]2)=[O:18]>[C].[Pd].C(N(CC)CC)C>[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[S@:17]([CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]2)=[O:18]

Participants

5

Reactant 2

HCID 702EthanolHCID 19432929HCID 19432929, compound

Product 1

HCID 9866215161190-38-1Yield 131.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

In a pressure glass reactor containing ethanol was placed 12 g of 6-{3-[1-(2-methyl-4-bromophenyl)-2-imidazolylsulfinyl]propoxy}-3,4-dihydrocarbostyril. To the resulting solution were added 18 ml of triethylamine and 6 g of a 10% palladium carbon powder. The reactor inside was purged with hydrogen gas and the reactor contents were subjected to a reaction at a pressure of 3 kg/cm2 at 70° C. for 16 hours. The reaction was repeated on the same scale. The reaction mixture obtained from two times of the reaction was filtered to remove the catalyst. The filtrate was extracted with chloroform, washed with 1 N aqueous hydrochloric acid solution thoroughly, washed with an aqueous solution saturated with sodium chloride, dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent. The resulting white oil was purified by a silica gel column chromatography (eluant: dichloromethane/ethyl acetate/methanol=30/10/1) to obtain crude crystals. The crude crystals were recrystallized from ethanol to obtain 13.2 g of (S)-(+)-6-{3-[1-(2-methylphenyl)-2-imidazolylsulfinyl]propoxy}-3,4-dihydrocarbostyril.

Workup

  1. customThe reactor inside was purged with hydrogen gas
  2. customthe reactor contents were subjected to a reaction at a pressure of 3 kg/cm2 at 70° C. for 16 hours
  3. customThe reaction mixture obtained from two times of the reaction
  4. filtrationwas filtered
  5. customto remove the catalyst
  6. extractionThe filtrate was extracted with chloroform
  7. washwashed with 1 N aqueous hydrochloric acid solution thoroughly
  8. washwashed with an aqueous solution saturated with sodium chloride
  9. dry with materialdried with anhydrous magnesium sulfate
  10. distillationsubjected to distillation
  11. customto remove the solvent
  12. customThe resulting white oil was purified by a silica gel column chromatography (eluant: dichloromethane/ethyl acetate/methanol=30/10/1)
  13. customto obtain crude crystals
  14. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-51502feef631467f99b352b3a6f0d087
Source dataset
uspto-grants-1996_07
Patent number
US05541198

Reaction notes

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