Lawesson's reagent → Tert-butyl 5-methyl-2-phenylthiazole-4-carboxylate

HRID 453285Notes

Reaction equation

HRID 453285 reaction equation
[C:1]([NH:9][CH:10]([C:18](=O)[CH3:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:30]2)=CC=1>C1COCC1>[CH3:19][C:18]1[S:30][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58551885Tert-butyl 2-benzamido-3-oxobutanoate

Product 1

HCID 67424508Tert-butyl 5-methyl-2-phenylthiazole-4-carboxylateYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 2-benzamido-3-oxobutanoate (842 mg, 3.04 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) (1.88 g 6.07 mmol) in THF (20 ml) was heated at reflux for 6 h. The mixture was evaporated in vacuo and purified by flash chromatography to give tert-butyl 5-methyl-2-phenylthiazole-4-carboxylate as a yellow solid (520 mg, 62% yield).

Workup

  1. temperatureat reflux for 6 h
  2. customThe mixture was evaporated in vacuo
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-ec0cce1d1a024bdab1c32c04a1c2a498
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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