Potassium Carbonate → HCID 23042045, compound

HRID 2166092Notes

Reaction equation

HRID 2166092 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[F:8][C:9]([F:19])([F:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][NH2:17].[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:22]=1[C:23](F)=[O:24].[OH-].[Ca+2].[OH-]>O.C(OCC)(=O)C>[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:22]=1[C:23]([NH:17][NH:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([F:18])([F:19])[F:8])=[O:24]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 6093208Calcium HydroxideHCID 12891828[2-(Trifluoromethyl)phenyl]hydrazine--hydrogen chloride (1/1)HCID 217311632,6-Difluorobenzoyl fluoride

Product 1

HCID 23042045HCID 23042045, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
3 °C

Procedure

13.6 g (98 mmol) of potassium carbonate in 70 ml of water are added at 10° C. while stirring to a suspension of 10.4 g (49 mmol) of α,α,α-trifluoro-o-tolylhydrazine hydrochloride in 50 ml of ethyl acetate. 7.8 g (49 mmol) of 2,6-difluorobenzoyl fluoride are subsequently added dropwise to the clear solution while cooling so that the internal temperature is maintained at 3° C. The mixture is stirred at 5° C. for 60 minutes and thereafter at 25° C. for 4 hours, and the organic phase is separated. The aqueous phase is back-extracted with 50 ml of ethyl acetate and subsequently treated with 1.85 g (25 mmol) of calcium hydroxide in order to precipitate the calcium fluoride. The combined organic phases are washed in each case once with dilute hydrochloric acid and sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After recrystallization from acetone and n-hexane there is obtained 2,6-difluoro-N' -(α,α,α-trifluoro-o-tolyl)-benzhydrazide as a white crystallizate, m.p. 129°-130° C.; mass spectrum m/e: M+ 316(26), 141(100).

Workup

  1. temperaturewhile cooling so that the internal temperature
  2. waitat 25° C. for 4 hours
  3. customthe organic phase is separated
  4. extractionThe aqueous phase is back-extracted with 50 ml of ethyl acetate
  5. customto precipitate the calcium fluoride
  6. washThe combined organic phases are washed in each case once with dilute hydrochloric acid and sodium bicarbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customAfter recrystallization from acetone and n-hexane

Sources & evidence

ORD record
ord-188253962fee4288829418d5ae86ee68
Source dataset
uspto-grants-1990_07
Patent number
US04943583

Reaction notes

Loading…