Pyridine → HCID 13805985, compound

HRID 2292022Notes

Reaction equation

HRID 2292022 reaction equation
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].[CH3:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]([CH3:18])=[CH:13][S:12]1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH3:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]([CH3:18])=[C:13]([CH:22]2[CH:23]=[CH:24][N:19]([C:5]([O:4][CH2:3][C:2]([Cl:9])([Cl:8])[Cl:1])=[O:6])[CH:20]=[CH:21]2)[S:12]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 13805967HCID 13805967, compound

Product 1

HCID 13805985HCID 13805985, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

2,2,2-Trichloroethylchloroformate (1.68 ml) was added dropwise to a solution of 2,5-dimethyl-2H-1,4-thiazin-3(4H)-one (1.43 g) and pyridine (1.6 ml) in acetonitrile (50 ml) under ice-cooling, and the solution was stirred for 30 minutes at 0° C. The mixture was further stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure. The residue was extracted with chloroform, was washed with 2N hydrochloric acid and successively with water and was dried over magnesium sulfate. The solvent was removed and the residue was chromatographed on silica gel (Wakogel C-200) column, using ethyl acetate-n-hexane (=1:1) as an eluant. The eluate was washed with ether to give the titled compound (1.68 g, yield 42%) as pale yellow crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture was further stirred at ambient temperature for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. extractionThe residue was extracted with chloroform
  5. washwas washed with 2N hydrochloric acid and successively with water
  6. dry with materialwas dried over magnesium sulfate
  7. customThe solvent was removed
  8. customthe residue was chromatographed on silica gel (Wakogel C-200) column
  9. washThe eluate was washed with ether

Sources & evidence

ORD record
ord-a4f5087f3de3449b86ed1e5c254dbe55
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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