Ethanethiol → HCID 19030945, compound

HRID 266820Notes

Reaction equation

HRID 266820 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-8e562b09197f42cbb302ffe5d3c18ba4
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

Loading…