3-Pyridinecarboxaldehyde → 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-3-formyl-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one

HRID 2292008Notes

Reaction equation

HRID 2292008 reaction equation
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[O:17])[CH:11]=1.[CH3:18][C:19]1[NH:20][C:21](=[O:25])[CH2:22][S:23][CH:24]=1>C(#N)C>[CH3:18][C:19]1[NH:20][C:21](=[O:25])[CH2:22][S:23][C:24]=1[CH:13]1[CH:14]=[CH:15][N:10]([C:5]([O:4][CH2:3][C:2]([Cl:9])([Cl:8])[Cl:1])=[O:6])[CH:11]=[C:12]1[CH:16]=[O:17]

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 870632,2,2-Trichloroethyl chloroformateHCID 2900175-Methyl-2h-1,4-thiazin-3(4h)-one

Product 1

HCID 136724205-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-3-formyl-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-oneYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,2,2-Trichloroethylchloroformate (2.13 ml) was added dropwise to a solution of pyridine-3-aldehyde (1.66 g) in dry acetonitrile (50 ml) under ice-cooling, and the mixture was stirred for 0.5 hour. 5-Methyl-2H-1,4-thiazin-3(4H)-one (1.0 g) was added to the mixture. The reaction mixture was further stirred at ambient temperature for 1 hour. The solvent was removed under reduced pressure. The residue was chromatographed on silica gel (Wakogel C-200) column, using ethyl acetate-n-hexane (=1:1) as an eluant. The eluant was recrystallized from ethanol to give the titled compound (1.4 g, yield 44%) as pale yellow crystals.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was further stirred at ambient temperature for 1 hour
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was chromatographed on silica gel (Wakogel C-200) column
  5. customThe eluant was recrystallized from ethanol

Sources & evidence

ORD record
ord-c77b3af3aa0247b69b1a29687074926c
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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