Acetic Acid → HCID 21188133, compound

HRID 1421279Notes

Reaction equation

HRID 1421279 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][NH2:14].[C:15]([CH2:23][C:24]#[N:25])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C>C(O)C>[NH2:25][C:24]1[N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][C:4]=2[Cl:12])[N:14]=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 64799BenzoylacetonitrileHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

Product 1

HCID 21188133HCID 21188133, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2,6-dichloro-4-trifluoromethylphenylhydrazine (0.245 g) in ethanol (2 ml) was added to a stirred solution of benzoylacetonitrile (0.145 g) in ethanol (8 ml) and the resulting solution heated under reflux for 6 hours. Glacial acetic acid (1 ml) was added and the resulting mixture heated under reflux for a further 6 hours and then evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (10 g), using dichloromethane as eluant, followed by reverse phase HPLC on C18 silica, using acetonitrile:methanol:water (50:10:40) as eluant, to afford the title compound as a white solid, m.p. 141.5-142.5° C. δ(CDCl3): 3.60 (br.s,2H), 6.08 (s,1H), 7.30-7.45 (m,3H), 7.80 (s,2H), 7.80-7.85 (m,2H). MS (thermospray): M/Z [M+H] 372.1; C16H10Cl2F3N2 +H requires 372.03.

Workup

  1. temperaturethe resulting solution heated
  2. temperatureunder reflux for 6 hours
  3. temperaturethe resulting mixture heated
  4. temperatureunder reflux for a further 6 hours
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (10 g)

Sources & evidence

ORD record
ord-38456eb26a9f4d3bbc1581f95450a3e3
Source dataset
uspto-grants-2000_06
Patent number
US06075043

Reaction notes

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