Acetonitrile → HCID 13457213, compound

HRID 462456Notes

Reaction equation

HRID 462456 reaction equation
C([N:4]([C:6](=O)[CH2:7][O:8][CH2:9][C:10]1[NH:11][C:12]([CH3:33])=[C:13]([C:29]([O:31][CH3:32])=[O:30])[CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=2[Cl:28])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH2:5])(=O)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:44])=CC=1.[C:57](#N)[CH3:58]>>[Cl:28][C:22]1[C:23]([Cl:27])=[CH:24][CH:25]=[CH:26][C:21]=1[CH:14]1[C:13]([C:29]([O:31][CH3:32])=[O:30])=[C:12]([CH3:33])[NH:11][C:10]([CH2:9][O:8][CH2:7][C:6]2[S:44][C:57]([CH3:58])=[N:5][N:4]=2)=[C:15]1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 87949Lawesson's reagentHCID 70466347HCID 70466347, compound

Product 1

HCID 13457213HCID 13457213, compound

Procedure

A mixture of 1-acetyl-2-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetylhydrazine (1.50 g) and Lawesson's reagent (1.18 g) in acetonitrile (50 ml) was stirred at room temperature for 24 hours and then evaporated. The residue was purified by chromatography on silica (t.l.c. grade, 20 g) using dichloromethane plus 40% v/v n-hexane followed by dichloromethane plus 0-1% v/v methanol as eluant. Appropriate fractions were combined and evaporated and residual oil triturated with diethyl ether. The resulting solid was collected, washed with diethyl ether and dried to give the title compound (0.82 g), m.p. 140°-144° C.

Workup

  1. customevaporated
  2. customThe residue was purified by chromatography on silica (t.l.c. grade, 20 g)
  3. customevaporated
  4. customresidual oil triturated with diethyl ether
  5. customThe resulting solid was collected
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-7e3da52c0509466d94f6950d185bdc16
Source dataset
uspto-grants-1985_05
Patent number
US04515799

Reaction notes

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