Hydrogen Sulfide → 2-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-thioacetamide

HRID 1433072Notes

Reaction equation

HRID 1433072 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]#[N:21])[CH2:15][CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:22]=1.C(N(C(C)C)CC)(C)C.[SH2:32]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:14][CH2:15][N:16]([CH2:19][C:20]([NH2:21])=[S:32])[CH2:17][CH2:18]3)(=[O:11])=[O:12])[S:7][C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 81531DiisopropylethylamineHCID 86592559[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-acetonitrile

Product 1

HCID 865925602-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-thioacetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-acetonitrile (1.2 g, 3.2 mmol) is heated with diisopropylethylamine (0.65 g, 5.0 mmol) in a solution of ethanol saturated with hydrogen sulfide gas for 4 hours. The reaction is cooled, filtered and washed with cold ethanol to provide 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-thioacetamide. 1H NMR (300 MHz, DMSO-d6) δ9.71 (bs, 1H), 9.01 (bs, 1H), 8.35 (d, 1H), 8.21 (s, 1H), 8.08 (d, 1H), 7.59 (dd, 1H), 4.15 (s, 2H), 3.73 (s, 2H), 3.43 (s, 4H).

Workup

  1. temperatureThe reaction is cooled
  2. filtrationfiltered
  3. washwashed with cold ethanol

Sources & evidence

ORD record
ord-be1e9c28a1b24a9192992e71e5d14a5a
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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