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

HRID 1381901ノート

反応式

HRID 1381901 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-340368a6d3b84bbea1772620aeb1dd0c
出典データセット
uspto-grants-1989_02
特許番号
US04804668

反応ノート

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