Ethanol, 1-ethoxy-2,2,2-trifluoro- → Trifluoroacetaldehyde {2-chloro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}hydrazone

HRID 253321Notes

Reaction equation

HRID 253321 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[NH:15][NH2:16].C(O[CH:20](O)[C:21]([F:24])([F:23])[F:22])C>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:13])([F:14])[F:12])=[CH:4][C:3]=1[NH:15][N:16]=[CH:20][C:21]([F:24])([F:23])[F:22]

Participants

5

Reactant 2

HCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 668419362-Chloro-4-methyl-5-(2,2,2-trifluoroethylthio)phenylhydrazine

Product 1

HCID 86628937Trifluoroacetaldehyde {2-chloro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}hydrazoneYield 67.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.1 g of 2-chloro-4-methyl-5-(2,2,2-trifluoroethylthio)phenylhydrazine, 2.3 g of trifluoroacetaldehyde ethyl hemiacetal, 0.1 g of p-toluenesulfonic acid monohydrate and 50 ml of ethanol was refluxed with heating for 6 hours. The obtained reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with toluene. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 3.6 g of trifluoroacetaldehyde {2-chloro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}hydrazone.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 6 hours
  3. customThe obtained reaction mixture
  4. concentrationwas concentrated under reduced pressure, water
  5. additionwas added
  6. extractionthe mixture was extracted with toluene
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6cb27ba9bd1347ed8de689626fd87816
Source dataset
uspto-grants-2011_01
Patent number
US07872036B2

Reaction notes

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