Sodium Hydroxide → HCID 86711823, compound

HRID 623734Notes

Reaction equation

HRID 623734 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:10]([C:11]([F:14])([F:13])[F:12])=[C:9]([CH3:15])[C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:7]1[C:23]([O:25]CC)=[O:24].[OH-].[Na+]>O.CCO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:10]([C:11]([F:13])([F:12])[F:14])=[C:9]([CH3:15])[C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:7]1[C:23]([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86711824HCID 86711824, compound

Product 1

HCID 86711823HCID 86711823, compoundYield 112.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of ethyl 1-(3-chlorobenzyl)-3-(4-chlorophenyl)-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (737 mg, 1.6 mmol) in H2O (10 mL) and EtOH (10 mL) was added NaOH (1.29 g, 32 mmol) and the mixture stirred at reflux for 3 h. The reaction mixture cooled to room temperature and concentrated the next day. Aqueous 5N HCl was added and the solids which had been formed were filtered off and dried on air for 5 d to give 768 mg of compound ACI-05 as a yellow solid.

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated the next day
  3. additionAqueous 5N HCl was added
  4. customthe solids which had been formed
  5. filtrationwere filtered off
  6. customdried on air for 5 d

Sources & evidence

ORD record
ord-8d1feab893654551acbee9f947943865
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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