Ammonia → HCID 12888759, compound

HRID 1719682Notes

Reaction equation

HRID 1719682 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 (3×), 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 (3×)
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent evaporated
  8. customthe residue crystallised from acetonitrile

Sources & evidence

ORD record
ord-425a7dfad99b4addaa557df475f32748
Source dataset
uspto-grants-1985_09
Patent number
US04542131

Reaction notes

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