Pyridine → HCID 13805986, compound

HRID 2292024Notes

Reaction equation

HRID 2292024 reaction equation
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].[CH2:10]([CH:12]1[C:17](=[O:18])[NH:16][C:15]([CH3:19])=[CH:14][S:13]1)[CH3:11].[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH2:10]([CH:12]1[C:17](=[O:18])[NH:16][C:15]([CH3:19])=[C:14]([CH:23]2[CH:24]=[CH:25][N:20]([C:5]([O:4][CH2:3][C:2]([Cl:9])([Cl:8])[Cl:1])=[O:6])[CH:21]=[CH:22]2)[S:13]1)[CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 13805968HCID 13805968, compound

Product 1

HCID 13805986HCID 13805986, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

2,2,2-Trichloroethylchloroformate (1.0 ml) was added dropwise to a solution of 2-ethyl-5-methyl-2H-1,4-thiazin-3(4H)-one (0.94 g) and pyridine (0.96 ml) in acetonitrile (30 ml) under ice-cooling, and the mixture was stirred at 0° C. for 30 minutes. Then the mixture was further stirred at ambient temperature for 18 hours. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate, was washed with water, 2N hydrochloric acid and water in the order named, and was dried over magnesium sulfate. The solvent was removed under reduced pressure to give 2-ethyl-5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (2.0 g) as pale yellow oily product.

Workup

  1. temperaturecooling
  2. stirringThen the mixture was further stirred at ambient temperature for 18 hours
  3. customThe solvent was removed under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washwas washed with water, 2N hydrochloric acid and water in the order
  6. dry with materialwas dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-293904201ac9459fb07316eaf6cbb1b3
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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