Acetic Acid → HCID 178506288, compound

HRID 2072292Notes

Reaction equation

HRID 2072292 reaction equation
[F:1][C:2]([F:12])([F:11])[CH2:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].C(O)(=O)C.[N:17]([O-])=O.[Na+]>O>[F:1][C:2]([F:11])([F:12])[C:3]1[C:4]2[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:6][N:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 213271262-(2,2,2-Trifluoroethyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 178506288HCID 178506288, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18.9 parts of 2-(2,2,2-trifluoro-ethyl)-aniline are dissoved in 700 parts by volume of glacial acetic acid. 14 parts by volume of a 50% aqueous solution of sodium nitrite are poured at one go into this well stirred solution. The temperature of the mass rises from 20° C. 27° C. The stirring is maintained at ambient temperature for about 15 hours, after which the intermediate diazo derivative has totally disappeared. A large part of the acetic acid is eliminated by distillation in vacuum so as to give a volume of about 100 parts. Then the solution is run into 160 parts of cold water with stirring. The precipitate of 3-trifluoromethyl-indazole formed is filtered off and washed with water: crude M.p. 98° C. It is recrystallised from boiling water for analysis. White needles of M.p. 104° C. (Kofler stage) are obtained; dry weight after recrystallisation 11.4 parts.

Workup

  1. customrises from 20° C
  2. custom27° C
  3. distillationA large part of the acetic acid is eliminated by distillation in vacuum so as
  4. customto give a volume of about 100 parts
  5. stirringwith stirring

Sources & evidence

ORD record
ord-61f0af2dd7794036a9f3b8de3a252d4b
Source dataset
uspto-grants-1977_09
Patent number
US04051145

Reaction notes

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