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

HRID 1107581Notes

Reaction equation

HRID 1107581 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11](=[O:27])[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]4[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[CH2:21][CH2:20]4)=[CH:14][CH:13]=3)=[C:9]([C:28]3[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=3)[S:8][C:7]=2[CH:36]=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:27])[C:12]3[CH:13]=[CH:14][C:15]([O:18][CH:19]4[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[CH2:21][CH2:20]4)=[CH:16][CH:17]=3)=[C:9]([C:28]3[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=3)[S:8][C:7]=2[CH:36]=1

Participants

4

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 154621626-Methoxy-2-(4-Methoxyphenyl)-3-(4-[1-Ethylpiperidin-4-oxy]benzoyl)benzo[b]thiophene

Product 1

HCID 98476976-Hydroxy-2-(4-Hydroxyphenyl)-3-(4-[1-Ethylpiperidin-4-oxy]benzoyl)benzo[b]thiopheneYield 72%

Procedure

6-Methoxy-2-(4-methoxyphenyl)-3-(4-[1-ethylpiperidin-4-oxy]benzoyl)benzo[b]thiophene (502 mg, 1.00 mmol), ethane thiol (5.00 mmol), and aluminum chloride (800 mg, 6.00 mmol) were converted to 341 mg (72%) of the title compound by the procedure of Example 16. MS(FD) 571(M+). IR (CHCl3) ν max 3300, 2971, 1598, 1249, 1165.

Sources & evidence

ORD record
ord-02f9cb12ed834061bf795e5239067f96
Source dataset
uspto-grants-2000_05
Patent number
US06060488

Reaction notes

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