Lawesson's reagent → HCID 68407298, compound

HRID 2244426Notes

Reaction equation

HRID 2244426 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:13]#[N:14])[NH:6][C:7](=O)[CH2:8][CH2:9][O:10][CH3:11])[CH3:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:25]2)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[N:6]=[C:7]([CH2:8][CH2:9][O:10][CH3:11])[S:25][C:13]=1[NH2:14])=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86606570HCID 86606570, compound

Product 1

HCID 68407298HCID 68407298, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of cyano-(3-methoxy-propionylamino)-acetic acid ethyl ester (0.95 g, 4.44 mmol) in toluene (11.00 ml) was flushed with argon. 2,4-bis(4-Methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) (0.90 g, 2.22 mmol) was added at once and the mixture was warmed at 110° C. for 2 h. Toluene was evaporated and the residue purified by flash chromatography (heptane/ethyl acetate) to yield 5-amino-2-(2-methoxy-ethyl)-thiazole-4-carboxylic acid ethyl ester (0.42 g, 40%), MS (ISP): m/e=231.1 (M+H+).

Workup

  1. customwas flushed with argon
  2. customToluene was evaporated
  3. customthe residue purified by flash chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-a5a633ccb1584f0f9fea5c70fd1374cc
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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