Ethanethiol → 6-Hydroxy-3-[3-hydroxy-4-[(1-pyrrolidinyl)methyl]benzyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

HRID 1387093Notes

Reaction equation

HRID 1387093 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:13]([O:23]C)[CH:12]=3)=[C:8]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[CH:27][CH:26]=3)[S:7][C:6]=2[CH:39]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:13]([OH:23])[CH:12]=3)=[C:8]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[CH:27][CH:26]=3)[S:7][C:6]=2[CH:39]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 104824786-Hydroxy-3-(3-methoxy-4-((1-pyrrolidinyl)methyl)benzyl)-2-(4-(2-(1-pyrrolidinyl)ethoxy)phenyl)benzo(b)thiophene

Product 1

HCID 211826926-Hydroxy-3-[3-hydroxy-4-[(1-pyrrolidinyl)methyl]benzyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiopheneYield 95%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

6-Hydroxy-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (65 mg, 0.12 mmol) in dichloroethane (3 mL) was treated with ethanethiol (0.2 mL) and aluminum chloride (160 mg) at 0° C. for 2 h before quenching with saturated aqueous sodium bicarbonate solution (5 mL). The stirring was continued for 1 h at ambient temperature. The mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL) and extracted with dichloromethane (50 mL×3). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (5:5:90) afforded the title compound as a white foam (60 mg, 95%).

Workup

  1. custombefore quenching with saturated aqueous sodium bicarbonate solution (5 mL)
  2. additionThe mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL)
  3. extractionextracted with dichloromethane (50 mL×3)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e59708e7231846c3aaa3f0f8c6283fe5
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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