Water → 2-(4-Chloro-phenyl)-4-ethoxycarbonylmethyl-thiazole-5-carboxylic acid ethyl ester

HRID 554851Notes

Reaction equation

HRID 554851 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5](Cl)[C:6](=O)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[S:22])=[CH:19][CH:18]=1.O>CCO>[CH2:1]([O:3][C:4]([C:5]1[S:22][C:21]([C:20]2[CH:24]=[CH:25][C:17]([Cl:16])=[CH:18][CH:19]=2)=[N:23][C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 27348264-ChlorothiobenzamideHCID 866400012-Chloro-3-oxo-pentanedioic acid diethyl ester

Product 1

HCID 674592172-(4-Chloro-phenyl)-4-ethoxycarbonylmethyl-thiazole-5-carboxylic acid ethyl esterYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Dissolve 2-chloro-3-oxo-pentanedioic acid diethyl ester (1370 g, 5.50 mol) in EtOH (8.5 L) and add 4-chloro-thiobenzamide (885 g, 5.00 mol). Heat the mixture to 75° C. and stir mechanically for 5.5 h. Cool the mixture to 45° C., then slowly add water (3.5 L) and stir overnight. Collect the yellow precipitate and wash the solids with 50% EtOH/water (4 L). Dry in an oven to obtain 1505 g (81%) of the title compound. 1H NMR (CDCl3, 500 MHz): δ 7.90 (d, 2H, J=7.4), 7.41 (d, 2H, J=7.4), 4.34 (q, 2H, J=6.8), 4.24 (s, 2H), 4.19 (q, 2H, J=7.4), 1.36 (t, 3H, J=6.8), 1.27 (t, 3H, J=6.8).

Workup

  1. temperatureCool the mixture to 45° C.
  2. customCollect the yellow precipitate
  3. washwash the solids with 50% EtOH/water (4 L)
  4. customDry in an oven

Sources & evidence

ORD record
ord-9b9a9d94e51745ebb17ca2519d36efac
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

Loading…