Ethanethiol → HCID 19030945, compound

HRID 1708296Notes

Reaction equation

HRID 1708296 reaction equation
[CH2:1]([SH:3])[CH3:2].C[O-].[Na+].Br[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:36]=[CH:35][C:15]([C:16]([N:18]2[CH2:23][CH2:22][CH:21]([N:24]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:28][CH2:27][C:25]3=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:14][CH:13]=1>CO>[CH2:1]([S:3][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([N:18]2[CH2:23][CH2:22][CH:21]([N:24]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:28][CH2:27][C:25]3=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:35][CH:36]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 10942334Sodium MethoxideHCID 19030810HCID 19030810, compound

Product 1

HCID 19030945HCID 19030945, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethanethiol (0.125 ml) is dissolved in methanol (10 ml) and thereto is added sodium methoxide (0.11 g). The mixture is stirred at room temperature for 30 minutes. Thereto is added a solution of 1-{1-[4-(3-bromopropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.59 g) in methanol (2 ml) and the mixture is stirred at room temperature overnight. The solvent is concentrated and water is added to the residue, extracted with chloroform, dried with sodium carbonate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) to give 1-{1-[4-(3-ethylthiopropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.2 g).

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. concentrationThe solvent is concentrated
  3. additionwater is added to the residue
  4. extractionextracted with chloroform
  5. dry with materialdried with sodium carbonate
  6. distillationThe solvent is distilled off
  7. customthe resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-7ada74ee2f27448682d8db5c85b90b30
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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