Pyridine → HCID 13518417, compound

HRID 1285124Notes

Reaction equation

HRID 1285124 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:8])[CH2:5][S:6][CH:7]=1.Cl[C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH3:1][C:2]1[NH:3][C:4](=[O:8])[CH2:5][S:6][C:7]=1[CH:21]1[CH:22]=[CH:23][N:18]([C:10]([O:12][CH2:13][C:14]([Cl:17])([Cl:16])[Cl:15])=[O:11])[CH:19]=[CH:20]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 2900175-Methyl-2h-1,4-thiazin-3(4h)-one

Product 1

HCID 13518417HCID 13518417, compoundYield 31.5%

Procedure

To a solution of 5-methyl-2H-1,4-thiazin-3(4H)-one (1.5 g) in dry pyridine (20 ml), 2,2,2-trichloroethyl chloroformate (2.8 g) was added dropwise under ice bath temperature. The reaction mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and the residue was extracted with chloroform. The extract was washed with 2N hydrochloric acid and water, and dried over anhydrous magnesium sulfate and chloroform was removed under reduced pressure. The residual oil was triturated with ether and recrystallized from ethanol using decolorizing chacoal to give 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (1.4 g, yield 31.5%) as light yellow scales.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe extract was washed with 2N hydrochloric acid and water
  4. dry with materialdried over anhydrous magnesium sulfate and chloroform
  5. customwas removed under reduced pressure
  6. customThe residual oil was triturated with ether
  7. customrecrystallized from ethanol using

Sources & evidence

ORD record
ord-a613680879944d79b41486a3146b774b
Source dataset
uspto-grants-1986_01
Patent number
US04565813

Reaction notes

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