Water → HCID 21708411, compound

HRID 651422Notes

Reaction equation

HRID 651422 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH3:19])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:20](=[O:23])([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[CH3:19][N:8]([C:6]1[N:5]=[CH:4][N:3]=[C:2]([O:23][C:20]2[CH:14]=[CH:9][CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=2)[CH:7]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 21708388HCID 21708388, compound

Product 1

HCID 21708411HCID 21708411, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-6-(N-methyl-3-trifluoromethylanilino)-pyrimidine (0.30 g, 0.001 mol.) and sodium carbonate (0.28 g, 0.003 mol.) in DMF are stirred for 10 minutes. m-Trifluoro-methylphenol (0.16 g, 0.001 mol) is added and the mixture is heated to 60° C. for 12 hours. The mixture is then cooled and poured into water. The product is extracted into ethyl acetate, washed with 10% sodium hydroxide, 10% hydrochloric acid, and 5% potassium carbonate, dried over Na2SO4, filtered, and is concentrated under reduced pressure. 6-(N-methyl-3-trifluoromethylanilino)-4-(3-trifluoromethyl-phenoxy)pyrimidine (0.16 g) obtained by chromatography as a white solid. M.p. 118-119° C.

Workup

  1. temperatureThe mixture is then cooled
  2. extractionThe product is extracted into ethyl acetate
  3. washwashed with 10% sodium hydroxide, 10% hydrochloric acid, and 5% potassium carbonate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-38cfef40f77b4b03868558700e005ee7
Source dataset
uspto-grants-2001_08
Patent number
US06281219B1

Reaction notes

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