Lawesson's reagent → Ethyl thiazolo[4,5-c]pyridine-2-carboxylate

HRID 876800Notes

Reaction equation

HRID 876800 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C1(C)C=CC=CC=1>[S:25]1[C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N:8]=[C:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67306384Ethyl 2-(4-chloropyridin-3-ylamino)-2-oxoacetate

Product 1

HCID 65583458Ethyl thiazolo[4,5-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 2-(4-chloropyridin-3-ylamino)-2-oxoacetate (R-2) (8 g, 35 mmol) and Lawesson's reagent (8.5 g, 21 mmol) in toluene (100 mL) was refluxed for 2 h, and then concentrated in vacuo. The residue was purified by chromatography on silica gel to give the title compound. MS (m/z): 209 (M+1)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a916cb7f53ea4048be2db37d369d3409
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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