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

HRID 1107591Notes

Reaction equation

HRID 1107591 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:30])[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]4[N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:14][CH:13]=3)=[C:9]([C:31]3[CH:36]=[CH:35][C:34]([O:37]C)=[CH:33][CH:32]=3)[S:8][C:7]=2[CH:39]=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:30])[C:12]3[CH:13]=[CH:14][C:15]([O:18][CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]4[N:25]4[CH2:26][CH2:27][CH2:28][CH2:29]4)=[CH:16][CH:17]=3)=[C:9]([C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=3)[S:8][C:7]=2[CH:39]=1

Participants

4

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 99589906-Methoxy-2-(4-Methoxyphenyl)-3-(4-[2-Pyrrolidin-1-ylcyclohexoxy]benzoyl)benzo[b]thiophene

Product 1

HCID 187872946-Hydroxy-2-(4-Hydroxyphenyl)-3-(4-[2-Pyrrolidin-1-ylcyclohexoxy]benzoyl)benzo[b]thiopheneYield 92.6%

Procedure

6-Methoxy-2-(4-methoxyphenyl)-3-(4-[2-pyrrolidin-1-ylcyclohexoxy]benzoyl)benzo[b]thiophene (610 mg, 1.10 mmol), ethane thiol (5.50 mmol), and aluminum chloride (880 mg, 6.60 mmol) were converted to 523 mg (90%) of the title compound by the procedure of Example 16. MS(FD) 528(M+). IR (CHCl3) ν max 3377, 2934, 2857, 1595, 1467, 1258, 1164.

Sources & evidence

ORD record
ord-70e7b1a576664351a60eb5e12f6eb9bf
Source dataset
uspto-grants-2000_05
Patent number
US06060488

Reaction notes

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