Benzaldehyde Methylhydrazone → HCID 76657009, compound

HRID 1908689Notes

Reaction equation

HRID 1908689 reaction equation
[CH3:1][NH:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O[CH:14]=[C:15]([C:21](=[O:25])[CH:22]([F:24])[F:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>C1(C)C=CC=CC=1>[F:24][CH:22]([F:23])[C:21](=[O:25])[C:15](=[CH:14][N:2]([CH3:1])[N:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 302615Benzaldehyde MethylhydrazoneHCID 53395411Butanoic acid, 2-(ethoxymethylene)-4,4-difluoro-3-oxo-, ethyl ester

Product 1

HCID 76657009HCID 76657009, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

13.8 g (0.1 mol) of benzaldehyde methylhydrazone and 62.2 g of toluene were admixed with 23.7 g (0.1 mol) of ethyl 2-ethoxymethylene-4,4-difluoro-3-oxo-butyrate, as a result of which the internal temperature rose to 35° C. The reaction mixture was stirred at reflux temperature for 1.25 hours and then stirred at 25° C. for 15 hours. The precipitated solid was filtered off with a suction filter and washed twice with 25 m; each time of toluene. After drying at 40-50° C. under reduced pressure, 23 g of product were obtained.

Workup

  1. customas a result of which the internal temperature
  2. customrose to 35° C
  3. temperatureat reflux temperature for 1.25 hours
  4. stirringstirred at 25° C. for 15 hours
  5. filtrationThe precipitated solid was filtered off with a suction
  6. filtrationfilter
  7. washwashed twice with 25 m
  8. customAfter drying at 40-50° C. under reduced pressure

Sources & evidence

ORD record
ord-e8ea2ca0dd7c4b898f87d3385721cb98
Source dataset
uspto-grants-2013_12
Patent number
US08598222B2

Reaction notes

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