2-Bromo-1-(3-bromophenyl)ethan-1-one → ethyl 1-{[4-(3-bromophenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylate

HRID 1257338Notes

Reaction equation

HRID 1257338 reaction equation
[NH2:1][C:2](=[S:14])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[CH:20]=1)=O>C(O)C>[Br:25][C:21]1[CH:20]=[C:19]([C:17]2[N:1]=[C:2]([CH2:3][N:4]3[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]3)[S:14][CH:16]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-oneHCID 58127901Ethyl 1-(carbamothioylmethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 58127935ethyl 1-{[4-(3-bromophenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylateYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution (5 mL) of the compound (1.1 g, 5.16 mmol) obtained in Example 1b in ethanol was added 2-bromo-1-(3-bromophenyl)ethanone (1.6 g, 5.67 mmol), and the mixture was heated under reflux for 3 hr. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The obtained crude product was washed with ethyl acetate to give the title compound (1.44 g, 71%) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-4f492aa69777440e84057a2bb83e309d
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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