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

HRID 2368287Notes

Reaction equation

HRID 2368287 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-fa96c1b3e1a34baf851be7c36c98dff5
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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