Hydrochloric Acid → HCID 73412136, compound

HRID 421051Notes

Reaction equation

HRID 421051 reaction equation
C[O:2][C:3](=[O:32])[C:4]([C:30]#[N:31])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[C:13](=[O:29])[NH:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1.[OH-].[Na+].Cl>C(O)C>[F:22][C:21]([F:23])([F:24])[C:19]1[CH:20]=[C:15]([NH:14][C:13]([C:7]2[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:6]=2[CH:5]=[C:4]([C:30]#[N:31])[C:3]([OH:32])=[O:2])=[O:29])[CH:16]=[C:17]([C:25]([F:27])([F:28])[F:26])[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86595532HCID 86595532, compound

Product 1

HCID 73412136HCID 73412136, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-({N-[3,5-Bis(trifluoromethyl)phenyl]carbamoyl}-4 hydroxyphenyl)-2-cyanoacrylic acid methyl ester (50 mg, 0.11 mmol) was dissolved in ethanol (5 mL). 2 N sodium hydroxide (0.11 ml, 0.22 mmol) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was recrystallized (ethyl acetate) to give the title compound (13.5 mg, 30.4%) as a light yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas recrystallized (ethyl acetate)

Sources & evidence

ORD record
ord-3f5f41ca76164d2e9d7ccd9c5fb04a68
Source dataset
uspto-grants-2012_01
Patent number
US08097759B2

Reaction notes

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