Thiourea → Diethyl 2-amino-1,3-thiazole-4,5-dicarboxylate

HRID 1948371

Reaction equation

HRID 1948371 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Cl[CH:6]([C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C.O>[NH2:1][C:2]1[S:3][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:4]=1

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 10998635Diethyl 2-chloro-3-oxobutanedioate

Product 1

HCID 226556Diethyl 2-amino-1,3-thiazole-4,5-dicarboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of thiourea (1.7 g, 22 mmol) and diethyl 2-chloro-3-oxosuccinate (5.0 g, 22 mmol) in absolute ethanol (50 mL) was heated at reflux for one hour. After cooling to room temperature the solvent was removed leaving a white solid. The solid was dissolved in water (100 mL) and the resulting precipitate was filtered and dried (4.6 g, 87%). MS (ES): 245;

Workup

  1. temperatureat reflux for one hour
  2. customwas removed
  3. customleaving a white solid
  4. filtrationthe resulting precipitate was filtered
  5. customdried (4.6 g, 87%)

Sources & evidence

ORD record
ord-dc5f69a55f5c4c5b8c318282b64cb020
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Linked notes

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