Hydrochloric Acid → HCID 178492219, compound

HRID 1031946Notes

Reaction equation

HRID 1031946 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:13][CH2:12][C:11]([NH2:14])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22](N)=[CH:21][CH:20]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>CCOCC>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:13][CH2:12][C:11]([NH:14][C:22]3[CH:24]=[CH:25][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 7732P-AnisidineHCID 477954,5-Dihydro-1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine

Product 1

HCID 178492219HCID 178492219, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(3-trifluoromethylphenyl)-4,5-dihydro-1H-pyrazol-3-amine (0.23 g), 4-methoxyaniline (0.37 g) and p-toluenesulphonic acid (0.17 g) was heated in an oil bath at 140° under nitrogen for 15 minutes. The reaction was cooled, dilute hydrochloric acid and ether added and the organic phase separated, dried over sodium sulphate, filtered and evaporated to leave a yellow solid, which on trituration with pentane gave the colourless title compound (0.1 g) m.p. 127°-8°.

Workup

  1. temperaturewas heated in an oil bath at 140° under nitrogen for 15 minutes
  2. temperatureThe reaction was cooled
  3. customthe organic phase separated
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customto leave a yellow solid, which on trituration with pentane

Sources & evidence

ORD record
ord-f2a8fb11274f4eca81fbd9c79f49873a
Source dataset
uspto-grants-1990_09
Patent number
US04956378

Reaction notes

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