Diethyl bromomalonate → HCID 2744173, compound

HRID 977095Notes

Reaction equation

HRID 977095 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[S:6].Br[CH:12]([C:18](OCC)=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[S:6][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]([OH:19])[N:7]=2)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 69637Diethyl bromomalonateHCID 737238Benzenecarbothioamide, 3-chloro-

Product 1

HCID 2744173HCID 2744173, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

340 mg of 3-chlorothiobenzamide was dissolved in 10 ml of ethanol, 570 mg of diethyl bromomalonate was added to the solution, and the mixture was heated at 60° C. for 2 hours. After the reaction mixture was cooled, and the resulting crystal was collected by filtration and recrystallized from ethanol to give 408 mg of ethyl 2-(3-chlorophenyl)-4-hydroxy-5-thiazolecarboxylate. This product was hydrolyzed by a conventional process to give 306 mg of 2-(3-chlorophenyl)-4-hydroxy-5-thiazolecarboxylic acid (yield: 60%).

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. filtrationthe resulting crystal was collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ab3a171755d64f6aae66dd1b1de045e2
Source dataset
uspto-grants-1997_03
Patent number
US05614520

Reaction notes

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