Acetic Acid → HCID 18980932, compound

HRID 482607Notes

Reaction equation

HRID 482607 reaction equation
CS(OCC(OCCC)(C)C(C1C=CC(Cl)=CC=1)=O)(=O)=O.C([O-])(=O)C.[Na+].C(O)(=O)C.O.NN.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[C:45]([CH3:50])([O:46][CH2:47][CH2:48][CH3:49])[CH2:44][N:43]([C:51]([NH2:53])=[O:52])[N:42]=2)=[CH:37][CH:36]=1.[F:54][C:55]([F:66])([F:65])[C:56]1[CH:61]=[CH:60][C:59](N=C=O)=[CH:58][CH:57]=1>CO>[F:54][C:55]([F:66])([F:65])[C:56]1[CH:61]=[CH:60][C:59]([NH:53][C:51]([N:43]2[CH2:44][C:45]([CH3:50])([O:46][CH2:47][CH2:48][CH3:49])[C:41]([C:38]3[CH:37]=[CH:36][C:35]([Cl:34])=[CH:40][CH:39]=3)=[N:42]2)=[O:52])=[CH:58][CH:57]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 517045Sodium AcetateHCID 18980941HCID 18980941, compoundHCID 18981012HCID 18981012, compound

Product 1

HCID 18980932HCID 18980932, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3.5 g (10 mmole) of 2-methanesulfonyloxymethyl-2-propoxy-4'-chloropropiophenone (Example 96e) in 25 ml of methanol was added 1.5 g (18 mmole) of anhydrous sodium acetate, 2.5 g (41 mmole) of acetic acid and 1.0 g (20 mmole) of hydrazine monohydrate. The mixture was refluxed for one hour, concentrated in vacuo, partitioned between diethyl ether and water. The organic layer was washed with dilute aqueous sodium hydroxide and brine and then dried over anhydrous magnesium sulfate, filtered and concentrated to about 25 ml. To this solution of 3-(4-chlorophenyl)-4-methyl-4-propoxy-4,5-dihydro-1H-pyrazole-1-carboxamide was added 2.1 g (11 mmole) of 4-(trifluoromethyl)phenylisocyanate. After stirring for 1 hour the precipitated solid was filtered and washed with diethyl ether and hexanes yielding 3.3 g of the title compound, a white solid, mp 135°-138° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. concentrationconcentrated in vacuo
  3. custompartitioned between diethyl ether and water
  4. washThe organic layer was washed with dilute aqueous sodium hydroxide and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to about 25 ml
  8. filtrationwas filtered
  9. washwashed with diethyl ether and hexanes yielding 3.3 g of the title compound

Sources & evidence

ORD record
ord-1b21caf811bc4a7ab6f3ce061544b129
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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