Chloroacetone → 2-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-4-methylthiazole

HRID 462452Notes

Reaction equation

HRID 462452 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][C:22]([NH2:24])=[S:23])=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26].Cl[CH2:31][C:32](=O)[CH3:33]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][C:22]2[S:23][CH:31]=[C:32]([CH3:33])[N:24]=2)=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 134572282-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}-thioacetamide

Product 1

HCID 134572062-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-4-methylthiazoleYield 16.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}-thioacetamide (0.44 g) and chloroacetone (0.30 g) in ethanol (30 ml) was heated under reflux for 7 hours and then evaporated. The residual oil was purified by chromatography on silica (t.l.c. grade, 10 g) using dichloromethane plus 0-10% v/v ethyl acetate as eluant. Appropriate fractions were combined and evaporated and the residue triturated with diisopropyl ether. The resulting solid was collected, washed with petroleum ether (b.p. 60°-80° C.) and dried to give the title compound (78 mg), m.p. 107°-110° C.

Workup

  1. temperatureunder reflux for 7 hours
  2. customevaporated
  3. customThe residual oil was purified by chromatography on silica (t.l.c. grade, 10 g)
  4. customevaporated
  5. customthe residue triturated with diisopropyl ether
  6. customThe resulting solid was collected
  7. washwashed with petroleum ether (b.p. 60°-80° C.)
  8. customdried

Sources & evidence

ORD record
ord-8a0d1b504b2a42f288106f9fe3f197c6
Source dataset
uspto-grants-1985_05
Patent number
US04515799

Reaction notes

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