Hydrochloric Acid → HCID 15294979, compound

HRID 2259218Notes

Reaction equation

HRID 2259218 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=3)=[O:12])=[C:9]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[S:8][C:7]=2[CH:30]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.Cl.C(=O)(O)[O-].[Na+]>ClCCl.O.C1COCC1>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:17][CH:18]=3)=[O:12])=[C:9]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[S:8][C:7]=2[CH:30]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 19424255HCID 19424255, compound

Product 1

HCID 15294979HCID 15294979, compoundYield 62.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

35 mg of (6-methoxy-2-cyclopentylbenzo[b]thien-3-yl)[4-[2-(dimethylamino)ethoxy]phenyl]methanone was dissolved in 5 ml of dichloromethane, 65 mg of aluminum chloride and 0.03 ml of ethanethiol were added, and the mixture was stirred at room temperature for 2 hours. 0.3 ml of THF, 0.075 ml of 20% hydrochloric acid and 0.3 ml of water were added to the reaction mixture, a saturated aqueous sodium bicarbonate solution was added to make the mixture alkaline, and the resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off, and the resultant crude product was purified by TLC (developing solvent, chloroform:methanol=19:1) to obtain 21 mg of (6-hydroxy-2-cyclopentylbenzo[b]thien-3-yl)[4-[2-(dimethylamino)ethoxy]phenyl]methanone.

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customthe resultant crude product was purified by TLC (developing solvent, chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-c5c80bcb80ab4e329eb77c8ba96fd432
Source dataset
uspto-grants-1995_12
Patent number
US05472962

Reaction notes

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