Lawesson's reagent → Ethyl 5-amino-2-phenyl-1,3-thiazole-4-carboxylate

HRID 467690Notes

Reaction equation

HRID 467690 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]#[N:7])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[N:8]=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:27][C:6]=1[NH2:7])=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 3844040HCID 3844040, compound

Product 1

HCID 13514498Ethyl 5-amino-2-phenyl-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of benzoylamino-cyano-acetic acid ethyl ester (400 mg, 1.7 mmol) in toluene (4 ml) was flushed with argon, and Lawesson's reagent (314 mg, 0.85 mmol) was added. The reaction mixture was stirred at 100° C. for 5 days. The solvent was evaporated, and the product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as yellow solid (147 mg, 34%).

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe product was obtained
  4. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-485294dc345140a19bd970ac2edde07e
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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