2,2,2-Trifluoroethylhydrazine → 3,5-Bis(2-hydroxyphenyl)-1-(2,2,2-trifluoroethyl)-1h-[1,2,4]triazole

HRID 1358508Notes

Reaction equation

HRID 1358508 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](=O)[N:13]=1.[F:19][C:20]([F:25])([F:24])[CH2:21][NH:22][NH2:23]>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([C:11]2[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=2[OH:9])[N:22]([CH2:21][C:20]([F:25])([F:24])[F:19])[N:23]=1

Participants

4

Reactant 2

HCID 787402,2,2-TrifluoroethylhydrazineHCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 1358174593,5-Bis(2-hydroxyphenyl)-1-(2,2,2-trifluoroethyl)-1h-[1,2,4]triazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.38 g of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one boiled under reflux for 0.5 h with 1.6 ml of 2,2,2-trifluorethylhydrazine in 20 ml of ethanol. The mixture is cooled, poured onto water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated on a rotary evaporator. The residue is crystallized from methanol/water. After drying, 3,5-bis(2-hydroxyphenyl)-1-(2,2,2-trifluoroethyl)-1H-[1,2,4]triazole remains as colorless crystals of m.p. 154-156° C.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue is crystallized from methanol/water
  7. customAfter drying

Sources & evidence

ORD record
ord-c6c613738ae04f45998eb6d887d1de14
Source dataset
uspto-grants-2003_07
Patent number
US06596750B2

Reaction notes

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