Ammonia → HCID 12888759, compound

HRID 1995280Notes

Reaction equation

HRID 1995280 reaction equation
[NH2:1][C:2]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:9]([C:10](OCC)=[O:11])=[CH:8][N:7]([CH3:15])[N:6]=1.C(O)(C)C.N.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>C1(OC)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([C:10]([C:9]2[C:5]([NH:4][C:3]3[CH:16]=[CH:17][C:18]([C:20]([F:22])([F:21])[F:23])=[CH:19][C:2]=3[NH2:1])=[N:6][N:7]([CH3:15])[CH:8]=2)=[O:11])[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 3776IsopropanolHCID 531671-MethylpiperazineHCID 14590611HCID 14590611, compound

Product 1

HCID 12888759HCID 12888759, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 7519AnisoleSolvent2×

Conditions

Temperature
65 °C

Procedure

Ethyl 3-(2-amino-4-trifluoromethylanilino)-1-methylpyrazole-4-carboxylate (4.75 g) was stirred in a mixture of N-methylpiperazine (25 ml) and anisole (65 ml). A solution of titanium tetrachloride (4.2 ml) in anisole (20 ml) was added and the mixture was stirred under nitrogen at 65° C. for 30 minutes. A mixture of isopropanol (25 ml) and 0.88 ammonia solution (25 ml) was added and the stirred mixture cooled to 25° C. The precipitate was removed by filtration, washing with ethyl acetate. The combined filtrates were washed with water (3X), dried over magnesium sulphate, the solvent evaporated and the residue crystallised from acetonitrile to give the title compound m.p. 170° C.

Workup

  1. additionwas added
  2. temperaturethe stirred mixture cooled to 25° C
  3. customThe precipitate was removed by filtration
  4. washwashing with ethyl acetate
  5. washThe combined filtrates were washed with water (3X)
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent evaporated
  8. customthe residue crystallised from acetonitrile

Sources & evidence

ORD record
ord-7f3a0b5afe9046fa968a80ac11483292
Source dataset
uspto-grants-1983_09
Patent number
US04404137

Reaction notes

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