Hydrazine → HCID 86218864, compound

HRID 1973194Notes

Reaction equation

HRID 1973194 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]([F:25])([F:24])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:10]=1[C:11](O)=[O:12].[NH2:26][NH2:27]>CN(C)C=O.C(O)C>[F:5][C:6]([F:25])([F:24])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[C:10]=1[C:11]([NH:26][NH2:27])=[O:12]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 24386Thionyl ChlorideHCID 214931572,6-Bis(2,2,2-trifluoroethoxy)benzoic acid

Product 1

HCID 86218864HCID 86218864, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 702EthanolSolvent

Procedure

Thionyl cloride (11.9 g., 100 mmole), 2,6-di(2,2,2-trifluoroethoxy)benzoic acid (2.0 g., 6.3 mmole) and two drops of dimethyl formamide are heated to reflux temperature and maintained at reflux for 4 hours. Unreacted thionyl chloride is removed by distillation on a steam bath at water aspirator pressure. The residue is dissolved in dry tetrahydrofuran and added dropwise to a solution of 95 per cent hydrazine (3.2 g., 100 mmole) in ethanol (15 ml.). The mixture is allowed to sit overnight and evaporate to dryness. The residue is diluted with water and a white solid collected and purified by sublimation (138°-140°/0.2 to 0.5 mm. Hg.) followed by recrystallization from benzene to give 2,6-di-(2,2,2-trifluoroethoxy)benzoic acid hydrazide, m.p. 153°-154° C.

Workup

  1. temperatureto reflux temperature
  2. temperaturemaintained
  3. temperatureat reflux for 4 hours
  4. customUnreacted thionyl chloride is removed by distillation on a steam bath at water aspirator pressure
  5. dissolutionThe residue is dissolved in dry tetrahydrofuran
  6. customevaporate to dryness
  7. additionThe residue is diluted with water
  8. customa white solid collected
  9. custompurified by sublimation (138°-140°/0.2 to 0.5 mm. Hg.)
  10. customfollowed by recrystallization from benzene

Sources & evidence

ORD record
ord-0e26af9d2fc24384adfdc8a1bd3c040f
Source dataset
uspto-grants-1976_12
Patent number
US03996280

Reaction notes

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