Triethylamine → HCID 19847868, compound

HRID 2350934Notes

Reaction equation

HRID 2350934 reaction equation
[C:1]([N:4]=[C:5](OCC)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[Cl:13])(=O)[CH3:2].Cl.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][NH2:27].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:13][C:7]1[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=1[C:5]1[N:4]=[C:1]([CH3:2])[N:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([F:18])([F:29])[F:28])[N:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12891828[2-(Trifluoromethyl)phenyl]hydrazine--hydrogen chloride (1/1)HCID 19847783HCID 19847783, compound

Product 1

HCID 19847868HCID 19847868, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6.1 g (22 mmol) of ethyl N-acetyl-2-chloro-4-fluorobenzimidate and 6.7 g (25 mmol) of o-trifluoromethylphenylhydrazine hydrochloride in 100 ml of toluene is treated with 3.9 ml (28 mmol) of triethylamine and the whole is heated at reflux temperature for 18 hours. Thereafter, the reaction mixture is washed once with water and extracted twice with 50 ml of concentrated hydrochloric acid. The acidic aqueous phases are neutralized with ice-cold sodium hydroxide solution and extracted twice with diethyl ether, and the combined extracts are dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue is subjected to a bulb-tube distillation, the fractions with b.p. 200° C./0.01 mmHg (9.33 Pa) being collected and finally crystallized from diisopropyl ether/n-hexane. In this manner there is obtained 3-(2-chloro-4-fluorophenyl)-5-methyl-1-(α,α,α-trifluoro-o-tolyl)-1H-1,2,4-triazole, m.p. 116° C.; 1H--NMR (CDCl3, 60 MHz): 2.37 (s,CH3); mass spectrum: 335 (48), 314(43), 159(100).

Workup

  1. temperaturethe whole is heated
  2. temperatureat reflux temperature for 18 hours
  3. washThereafter, the reaction mixture is washed once with water
  4. extractionextracted twice with 50 ml of concentrated hydrochloric acid
  5. extractionextracted twice with diethyl ether
  6. dry with materialthe combined extracts are dried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue is subjected to a bulb-tube
  9. distillationdistillation
  10. customthe fractions with b.p. 200° C./0.01 mmHg (9.33 Pa) being collected
  11. customfinally crystallized from diisopropyl ether/n-hexane

Sources & evidence

ORD record
ord-e6b14690af644817ab80928874e9a3fe
Source dataset
uspto-grants-1989_10
Patent number
US04871757

Reaction notes

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