Tiopronin → 6-Methyl[1,4]thiazine-2,5-dione

HRID 35357ノート

反応式

HRID 35357 の反応式
[SH:1][CH:2]([CH3:10])[C:3]([NH:5][CH2:6][C:7](O)=[O:8])=[O:4].C(N(CC)CC)C.ClC(OCC)=O>C(Cl)Cl>[CH3:10][CH:2]1[S:1][C:7](=[O:8])[CH:6]=[N:5][C:3]1=[O:4]

参加物

5

反応物 3

HCID 5483TioproninHCID 8471TriethylamineHCID 10928Ethyl chloroformate

生成物 1

HCID 212963336-Methyl[1,4]thiazine-2,5-dione収率 33.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of N-(2-mercaptopropanoyl)glycine (5 g, 0.031 mole) in methylene chloride (250 ml) was chilled in an ice bath and triethylamine (3.1 g, 0.031 mole) was added. Ethyl chloroformate (3.4 g, 0.031 mole) in methylene chloride (25 ml) was added dropwise over 15 minutes. The resulting solution was then stirred for two and a half hours at room temperature. The methylene chloride was washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. Filtration and evaporation of the solvent afforded the crude product as a yellow oil which was chromatographed on silica-gel (CHCl3) to yield colorless crystals of 6-methyl[1,4]thiazine-2,5-dione (1.5 g, 30%) after crystallization from ether-hexane, m.p. 81°-83°.

後処理

  1. washThe methylene chloride was washed with water, saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and evaporation of the solvent
  4. customafforded the crude product as a yellow oil which
  5. customwas chromatographed on silica-gel (CHCl3)

出典と根拠

ORDレコード
ord-9df4d9e6e7a04af6a875e53b68f5ca95
出典データセット
uspto-grants-1988_08
特許番号
US04766210

反応ノート

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