2-Bromo-1-(3,4-dichlorophenyl)ethanone → HCID 58127540, compound

HRID 1257302Notes

Reaction equation

HRID 1257302 reaction equation
[CH:1]([CH:3]([CH:9]=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=O.[NH2:11][NH:12][C:13]([NH2:15])=[S:14].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)=O>C(O)C>[Cl:27][C:22]1[CH:21]=[C:20]([C:18]2[N:15]=[C:13]([N:12]3[CH:9]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:1]=[N:11]3)[S:14][CH:17]=2)[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

5

Reactant 3

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 2723789ThiosemicarbazideHCID 11029955Ethyl 2-formyl-3-oxopropanoate

Product 1

HCID 58127540HCID 58127540, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-formyl-3-oxopropanoate (0.57 g, 3.0 mmol) in ethanol (5 mL) was added thiosemicarbazide (1.37 g, 15 mmol), and the reaction mixture was stirred at room temperature for 1 hr. 2-Bromo-1-(3,4-dichlorophenyl)ethanone (0.54 g, 2.0 mmol) was added, and the mixture was stirred at 80° C. for 30 min, and cooled to room temperature. The precipitated crystals were collected by filtration to give the title compound (545 mg, 74%) as orange crystals.

Workup

  1. stirringthe mixture was stirred at 80° C. for 30 min
  2. temperaturecooled to room temperature
  3. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-2cda903accab4fe483c3061f42fe6705
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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