(Chlorothio)formyl chloride → Ethyl 2-hydroxy-4-methyl-1,3-thiazole-5-carboxylate

HRID 399190

Reaction equation

HRID 399190 reaction equation
Cl[C:2]([S:4]Cl)=[O:3].[NH2:6]/[C:7](/[CH3:14])=[CH:8]\[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C1(C)C=CC=CC=1>[CH3:14][C:7]1[NH:6][C:2](=[O:3])[S:4][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Product 1

HCID 11074139Ethyl 2-hydroxy-4-methyl-1,3-thiazole-5-carboxylateYield 62.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

25 g of chlorocarbonylsulphenyl chloride was added dropwise to 25 g of ethyl 3-aminocrotonate in 300 ml of toluene while being cooled with ice. The solution was heat-refluxed for 2 hours, and then cooled. The crystals precipitated were collected through filtration, and then washed twice with toluene to obtain 22.3 g of 4-methyl-5-ethoxycarbonyl-2-thiazolone as purple crystals.

Workup

  1. temperaturewhile being cooled with ice
  2. temperatureThe solution was heat-refluxed for 2 hours
  3. temperaturecooled
  4. customThe crystals precipitated
  5. filtrationwere collected through filtration
  6. washwashed twice with toluene

Sources & evidence

ORD record
ord-6ed8cb3f17d5497897d310ce6f90b851
Source dataset
uspto-grants-1998_10
Patent number
US05817829

Linked notes

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