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

HRID 1381901노트

반응식

HRID 1381901 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-340368a6d3b84bbea1772620aeb1dd0c
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04804668

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