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

HRID 1577108

반응식

HRID 1577108 반응식
[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]

참가 물질

5

반응물 3

HCID 5483TioproninHCID 8471TriethylamineHCID 10928Ethyl chloroformate

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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°.

후처리

  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)

출처 및 근거

ORD 기록
ord-9bdec28671664b01aa8db41627111eb1
출처 데이터셋
uspto-grants-1981_09
특허 번호
US04287203

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