Lawesson's reagent → 2-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}-thioacetamide

HRID 464638Notes

Reaction equation

HRID 464638 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])=O)=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>C(#N)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]([NH2:24])=[S:39])=[C:9]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 134572222-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetamide

Product 1

HCID 134572282-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}-thioacetamideYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetamide (6.8 g) and Lawesson's reagent (6.4 g) in acetonitrile (300 ml) was stirred at room temperature for 2.5 hours, filtered and evaporated. The residue was purified by chromatography on silica (80 g) using dichloromethane plus 0-10% v/v ethyl acetate as eluant. Appropriate fractions were combined and evaporated and the residual oil triturated with diethyl ether. The resulting solid was collected, washed with diethyl ether and dried to give the title compound (5.9 g), m.p. 149°-150° C. Found: C,54.38; H,5.29; N,6.37. C20H23ClN2O5S requires: C,54.74; H,5.28; N,6.38%.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was purified by chromatography on silica (80 g)
  4. customevaporated
  5. customthe residual oil triturated with diethyl ether
  6. customThe resulting solid was collected
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-f6c42ebb85584f26a7a5fe2504de77bf
Source dataset
uspto-grants-1985_10
Patent number
US04548935

Reaction notes

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