Thiazole → HCID 70393644, compound

HRID 2292020Notes

Reaction equation

HRID 2292020 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[S:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[CH3:12][C:13]1[NH:14][C:15](=[O:19])[CH2:16][S:17][CH:18]=1>ClCCl>[CH3:12][C:13]1[NH:14][C:15](=[O:19])[CH2:16][S:17][C:18]=1[CH:8]1[N:9]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][CH2:11][S:7]1

Participants

5

Reactant 3

HCID 9256ThiazoleHCID 10928Ethyl chloroformateHCID 2900175-Methyl-2h-1,4-thiazin-3(4h)-one

Product 1

HCID 70393644HCID 70393644, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethylchloroformate (3.6 g) was added dropwise to a solution of thiazole (5.7 g) in dichloromethane (72 ml) under ice-cooling, and the mixture was stirred for 30 minutes. Then, 5-methyl-2H-1,4-thiazin-3(4H)-one (3.6 g) was added dropwise to the mixture. The reaction mixture was further stirred at ambient temperature for 5 hours. The mixture was washed with 2N hydrochloric acid and successively with water, was dried over anhydrous magnesium sulfate and the solvent was removed. The residue was chromatographed on silica gel (Wakogel C-200) column, using ethyl acetate-n-hexane (=1:1) as an eluant and was recrystallized from ethanol to give the titled compound (1.9 g, yield 23.8%) as white needles.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was further stirred at ambient temperature for 5 hours
  3. washThe mixture was washed with 2N hydrochloric acid and successively with water
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customthe solvent was removed
  6. customThe residue was chromatographed on silica gel (Wakogel C-200) column
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-86fda96fee3247b3a124763ed371c48e
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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