Ethyl (chloroformyl)acetate → Ethyl 2-(4-chlorophenyl)-1,3-thiazole-5-carboxylate

HRID 1419692Notes

Reaction equation

HRID 1419692 reaction equation
[CH:1]([CH:3](Cl)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=O.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[S:16])=[CH:13][CH:12]=1>CCO>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]2[S:16][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:1][N:17]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 27348264-Chlorothiobenzamide

Product 1

HCID 53403642Ethyl 2-(4-chlorophenyl)-1,3-thiazole-5-carboxylateYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of ethyl formylchloroacetate (1.45 g, 9.6 mmol; obtained according to Panizzi, L. Gazz. Chim.Ital., 1946, 76, 56) and 4-chlorothiobenzamide (1.76 g, 9.6 mmol) in EtOH (50 mL) was refluxed for 48 h. The reaction mixture was then cooled to -20° C. and the solid formed was filtered and dried to give ethyl 2-(4-chlorophenyl)thiazole-5-carboxylate (0.59 g, 23%): mp 144°-145° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.40 (s, 1H, thiazole), 7.92 (dt, Jt =1.8, Jd =8.6, 2H, arom), 7.44 (dt, Jt =1.8, Jd =8.6, 2H, arom), 4.39 (q, J=7, 2H, OCH2), 1.40 (t, J=7, 3H, OCH2CH3). Analysis calculated for C12H10ClNO2S: C 53.84; H 3.76; N 5.23; S 11.97. Found: C 54.22; H 3.52; N 5.25; S 11.46.

Workup

  1. customthe solid formed
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-b99d651b7afb40849f14f1e5f1ac48ca
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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