Hydrochloric Acid → HCID 15294979, compound

HRID 741763Notes

Reaction equation

HRID 741763 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.CO.C(Cl)(Cl)Cl.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

11

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 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

35 mg of (6-methoxy-2-cyclopentylbenzo[b]thien-3-yl)[4-[2-(dimethylamino)ethoxy]phenyl]methanone is dissolved in 5 mL of dichloromethane, 65 mg of aluminum chloride and 0.03 mL of ethanethiol are added, and this mixture is agitated for two hours at room temperature. 0.3 mL of THF, 0.075 mL of 20% hydrochloric acid, and 0.3 mL of water are added to the reaction mixture, after which a saturated aqueous solution of sodium hydrogencarbonate is added to render the solution alkaline, and the organic layer is extracted with ethyl acetate and dried with anhydrous magnesium sulfate. The solvent is distilled off, and the crude product thus obtained is refined by TLC (developing solvent was chloroform:methanol=19:1), which gives 21 mg of (6-hydroxy-2-cyclopentylbenzo[b]thien-3-yl)[4-[2-(dimethylamino)ethoxy]phenyl]methanone.

Workup

  1. extractionthe organic layer is extracted with ethyl acetate
  2. dry with materialdried with anhydrous magnesium sulfate
  3. distillationThe solvent is distilled off
  4. customthe crude product thus obtained

Sources & evidence

ORD record
ord-1b89e85b58794883b740996ff2fb44db
Source dataset
uspto-grants-1996_09
Patent number
US05552433

Reaction notes

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