Hydrochloric Acid → HCID 18690191, compound

HRID 1872098Notes

Reaction equation

HRID 1872098 reaction equation
C(S)C.[H-].[Na+].[C:6]1([C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22]C)=[CH:19][CH:20]=3)[CH2:15][CH2:14][C:13]=2[C:24](=[O:33])[C:25]2[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>CN(C)C=O>[C:6]1([C:12]2[C:21]3[C:16](=[CH:17][C:18]([OH:22])=[CH:19][CH:20]=3)[CH2:15][CH2:14][C:13]=2[C:24](=[O:33])[C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 18690204HCID 18690204, compound

Product 1

HCID 18690191HCID 18690191, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a cold 300 mL of dimethylformamide and under a nitrogen atmosphere was added 9.3 g of ethylmercaptan. To this mixture was added 7.2 g of 50% sodium hydride (150 mmol) in oil. To this mixture was added 11.1 g (30 mmol) of 1-phenyl-2-(4-methoxybenzoyl)-3,4-dihydro-6-methoxynaphthalene and the reaction mixture was heated to 60° C. for two hours. The reaction was acidified with the addition of 1N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was washed with water and evaporated to dryness. The final product was crystallized from a mixture of methanol-acetone to yield 8 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. customevaporated to dryness
  5. customThe final product was crystallized from a mixture of methanol-acetone

Sources & evidence

ORD record
ord-3e7309a1ce35444f926e52a976f00d86
Source dataset
uspto-grants-2000_08
Patent number
US06107346

Reaction notes

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