Sodium ethoxide → HCID 15135628, compound

HRID 359482Notes

Reaction equation

HRID 359482 reaction equation
[SH:1][C:2]1[C:7]([C:8](=[O:14])[C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[O-]CC.[Na+].[CH3:19][N:20]([CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Cl>CN(C)C=O>[CH3:19][N:20]([CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:1][C:2]1[C:7]([C:8](=[O:14])[C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 129470316-Chloro-N,N-dimethylhexan-1-amineHCID 178519727HCID 178519727, compound

Product 1

HCID 15135628HCID 15135628, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 50 ml of dimethylformamide are added 4.4 g of 2-mercapto-3-(2-thenoyl)pyridine and 1.5 g of sodium ethoxide The mixture is stirred at room temperature for 30 minutes. Thereto, 4.0 g of 6-dimethylaminohexyl chloride is added, and the mixture is stirred at room temperature for 24 hours. The mixture is poured into ice-water, followed by extraction with toluene. The extract is washed with water, and the solvent is distilled. The residue is subjected to silica gel column chromatography with chloroform as the eluent, and recrystallized from isopropyl ether to give 2-(6-dimethylaminohexylthio)-3-(2-thenoyl)pyridine, m.p. 69°-71° C.

Workup

  1. stirringthe mixture is stirred at room temperature for 24 hours
  2. extractionfollowed by extraction with toluene
  3. washThe extract is washed with water
  4. distillationthe solvent is distilled
  5. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-341481700cf94fb4a249472b927c6f13
Source dataset
uspto-grants-1991_03
Patent number
US05001137

Reaction notes

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