Thiazole → 2,2-dimethoxy-5-methyl-6-(3-ethoxycarbonyl-2,3-dihydro-2-thiazolyl)-2H-1,4-thiazin

HRID 1381901Notes

Reaction equation

HRID 1381901 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[S:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[CH3:12][O:13][C:14]1([O:22][CH3:23])[C:19](=O)[NH:18][C:17]([CH3:21])=[CH:16][S:15]1>ClCCl>[CH3:23][O:22][C:14]1([O:13][CH3:12])[CH:19]=[N:18][C:17]([CH3:21])=[C:16]([CH:8]2[N:9]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH:10]=[CH:11][S:7]2)[S:15]1

Participants

5

Reactant 3

HCID 9256ThiazoleHCID 10928Ethyl chloroformateHCID 143697992,2-dimethoxy-5-methyl-4H-1,4-thiazin-3-one

Product 1

HCID 867427442,2-dimethoxy-5-methyl-6-(3-ethoxycarbonyl-2,3-dihydro-2-thiazolyl)-2H-1,4-thiazinYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroformate (1.0 g) was added dropwise to a stirred solution of thiazole (0.79 g) in dichloromethane (10 ml) under ice-cooling and the mixture was stirred at room temperature for 0.5 hour. Then, 2,2-dimethoxy-5-methyl-2H-1,4-thiazin-3(4H)-one (1.47 g) was added, and the mixture was stirred at room temperature for 3 hours. The solution was washed with saturated sodium bicarbonate aqueous solution, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel (Merck Lobar column size B: Art.10401, solvent: ethyl acetate-n-hexane=2:3) to give 2,2-dimethoxy-5-methyl-6-(3-ethoxycarbonyl-2,3-dihydro-2-thiazolyl)-2H-1,4-thiazin-(4H-one (510 mg, yield 19%) as colorless prisms.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. washThe solution was washed with saturated sodium bicarbonate aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel (Merck Lobar column size B: Art.10401, solvent: ethyl acetate-n-hexane=2:3)

Sources & evidence

ORD record
ord-340368a6d3b84bbea1772620aeb1dd0c
Source dataset
uspto-grants-1989_02
Patent number
US04804668

Reaction notes

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