Lawesson's reagent → Ethyl 5-amino-2-methylthiazole-4-carboxylate

HRID 2244459Notes

Reaction equation

HRID 2244459 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH:5]([C:10]#[N:11])[NH:6][C:7](=O)[CH3:8])[CH3:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:22]2)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[N:6]=[C:7]([CH3:8])[S:22][C:10]=1[NH2:11])=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 95422Ethyl acetamidocyanoacetate

Product 1

HCID 13329095Ethyl 5-amino-2-methylthiazole-4-carboxylateYield 100.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 2-acetylamino-cyanoacetic acid ethyl ester (1.70 g, 10.00 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) (2.02 g, 5.00 mmol) in toluene (25.00 ml) was heated under argon to 110° C. and stirred for 22 h. The solvent was then evaporated, and the residue purified by flash chromatography (heptane/ethyl acetate 1:1) to yield 5-amino-2-methyl-thiazole-4-carboxylic acid ethyl ester (0.94 g, 50.5%) as a yellow solid, MS (ISP): m/e=187.3 (M+H+).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue purified by flash chromatography (heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-5d735d0d98954448a936089d1c8cd431
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

Loading…