Potassium Hydroxide → HCID 58168875, compound

HRID 38766Notes

Reaction equation

HRID 38766 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[CH2:4][NH:5][C:6]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]([C:16]([O:18]C)=[O:17])=[CH:8][N:7]=1.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[CH2:4][NH:5][C:6]1[N:11]=[C:10]([C:12]([F:13])([F:15])[F:14])[C:9]([C:16]([OH:18])=[O:17])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58168975Methyl 2-(2,4-dichlorobenzylamino)-4-(trifluoromethyl)pyrimidine-5-carboxylate

Product 1

HCID 58168875HCID 58168875, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of methyl 2-(2,4-dichlorobenzylamino)-4-(trifluoromethyl)pyrimidine-5-carboxylate (443 mg) and ethanol (7 mL) was added a solution of potassium hydroxide (200 mg) in ethanol (4 mL), and the mixture was stirred under heating with reflux for 5 hours. The reaction liquid was concentrated under reduced pressure, water (70 mL) was added to the residue, and the liquid property was made acidic (pH 1) with concentrated hydrochloric acid. The product was extracted with ethyl acetate (200 mL) twice, and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 2-(2,4-dichlorobenzylamino)-4-(trifluoromethyl)pyrimidine-5-carboxylic acid (411 mg) as a colorless powder.

Workup

  1. temperatureunder heating
  2. temperaturewith reflux for 5 hours
  3. customThe reaction liquid
  4. concentrationwas concentrated under reduced pressure, water (70 mL)
  5. additionwas added to the residue
  6. extractionThe product was extracted with ethyl acetate (200 mL) twice
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2b07b3bd95004a3680d0552d5437b488
Source dataset
uspto-grants-2013_09
Patent number
US08524727B2

Reaction notes

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