Lawesson's reagent → 2-Methyl-5-phenylthiazole

HRID 2248967Notes

Reaction equation

HRID 2248967 reaction equation
[CH2:1]([NH:10][C:11](=O)[CH3:12])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:23]2)=CC=1>C1(C)C=CC=CC=1>[CH3:12][C:11]1[S:23][C:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:1][N:10]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 226684n-(2-Oxo-2-phenylethyl)acetamide

Product 1

HCID 123675102-Methyl-5-phenylthiazoleYield 31.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-phenacylacetamide (0.70 g, 4 mmol), 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide (Lawesson's reagent) (0.80 g, 2 mmol) and toluene (10 ml) was heated for 1.5 h at reflux and then evaporated under reduced pressure. The residue was purified by chromatography (10 g silica, dichloromethane) to give 2-methyl-5-phenylthiazole as a yellowish solid (0.11 g, 16%) m.p. 72°-4° C.; δH (CDCl3) 7.85(1H, S, CH), 7.3-7.7(5H, m, C6H5), 2.7(3H, S, CH3).

Workup

  1. temperaturewas heated for 1.5 h
  2. temperatureat reflux
  3. customevaporated under reduced pressure
  4. customThe residue was purified by chromatography (10 g silica, dichloromethane)

Sources & evidence

ORD record
ord-c2ed56b38ddb4c62af12325184587dad
Source dataset
uspto-grants-1991_08
Patent number
US05041567

Reaction notes

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