Acetic Acid → HCID 178481857, compound

HRID 1254969Notes

Reaction equation

HRID 1254969 reaction equation
[F:1][CH:2]([F:11])[C:3](=O)[CH2:4][C:5](OCC)=[O:6].C(O)(=O)C.[CH3:16][NH:17][NH2:18]>C(OC)(C)(C)C>[CH3:16][N:17]1[C:5]([OH:6])=[CH:4][C:3]([CH:2]([F:11])[F:1])=[N:18]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 67697Ethyl 4,4-difluoroacetoacetate

Product 1

HCID 178481857HCID 178481857, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
5 °C

Procedure

166 g (1 mol) of ethyl difluoroacetoacetate are initially charged in 500 ml of methyl tert-butyl ether, and 60 g of acetic acid are added. After the mixture has been cooled to 5° C., 119 g of methylhydrazine are added in 40% aqueous solution. The mixture is stirred at 22° C. for a further 20 h. The phases are separated, and the organic phase is washed with 200 ml of water and dried over MgSO4. After the solvent has been removed under reduced pressure, 140 g of the product are obtained as a yellow solid with an m.p. of 133° C. and a purity of 96%. Yield 91%.

Workup

  1. customThe phases are separated
  2. washthe organic phase is washed with 200 ml of water
  3. dry with materialdried over MgSO4
  4. customAfter the solvent has been removed under reduced pressure, 140 g of the product
  5. customare obtained as a yellow solid with an m.p. of 133° C.

Sources & evidence

ORD record
ord-850387ac8d2d4c15a70af626a39fd842
Source dataset
uspto-grants-2013_06
Patent number
US08455664B2

Reaction notes

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