Ethanethiol → 6-Hydroxy-2-(4-Hydroxyphenyl)-3-(4-[1-Benzylpyrrolidin-3-oxy]benzoyl)benzo[b]thiophene

HRID 1107587Notes

Reaction equation

HRID 1107587 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:31])[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]4[CH2:23][CH2:22][N:21]([CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:20]4)=[CH:14][CH:13]=3)=[C:9]([C:32]3[CH:37]=[CH:36][C:35]([O:38]C)=[CH:34][CH:33]=3)[S:8][C:7]=2[CH:40]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:31])[C:12]3[CH:13]=[CH:14][C:15]([O:18][CH:19]4[CH2:23][CH2:22][N:21]([CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:20]4)=[CH:16][CH:17]=3)=[C:9]([C:32]3[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=3)[S:8][C:7]=2[CH:40]=1

Participants

4

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 99155176-Methoxy-2-(4-Methoxyphenyl)-3-(4-[1-Benzylpyrrolidin-3-oxy]benzoyl)benzo[b]thiophene

Product 1

HCID 187872986-Hydroxy-2-(4-Hydroxyphenyl)-3-(4-[1-Benzylpyrrolidin-3-oxy]benzoyl)benzo[b]thiopheneYield 38%

Procedure

6-Methoxy-2-(4-methoxyphenyl)-3-(4-[1-benzylpyrrolidin-3-oxy]benzoyl)benzo[b]thiophene (1.57 g, 2.86 mmol), ethane thiol (14.3 mmol), and aluminum chloride (2.29 g, 17.2 mmol) were converted to 566 mg (38%) of the title compound by the procedure of Example 16. MS(FD) 521(M+). IR (CHCl3) ν max 3300, 3027, 3012, 2981, 1732, 1599, 1469, 1257, 1167.

Sources & evidence

ORD record
ord-52921904315942d8af1eff4a0e86650d
Source dataset
uspto-grants-2000_05
Patent number
US06060488

Reaction notes

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