Ammonium Acetate → HCID 22727016, compound

HRID 2085920Notes

Reaction equation

HRID 2085920 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9](=O)[CH:10]=[N:11][NH:12][C:13](=O)[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1.C([O-])(=O)C.[NH4+:27]>C(O)(=O)C>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[N:11][CH:10]=[C:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])[N:27]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 86587316HCID 86587316, compound

Product 1

HCID 22727016HCID 22727016, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.85 g of 4-bromobenzoic acid [2-(2,6-difluorophenyl)-2-oxoethylidene] hydrazide and 0.77 g of ammonium acetate is heated in 15 ml of glacial acetic acid at 10° C. for 14 h. After cooling to room temperature, the reaction mixture is poured into ice-water and extracted with ethyl acetate, and the organic phase is washed with saturated sodium hydrogen carbonate and saturated sodium chloride solution. After the organic phase has been dried over sodium sulfate, filtering and concentration in a rotary evaporator are carried out. The residue is purified by means of flash chromatography (5% ethyl acetate in toluene). In this way the title compound is obtained in the form of yellow crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase is washed with saturated sodium hydrogen carbonate and saturated sodium chloride solution
  3. dry with materialAfter the organic phase has been dried over sodium sulfate
  4. filtrationfiltering
  5. concentrationconcentration
  6. customin a rotary evaporator
  7. customThe residue is purified by means of flash chromatography (5% ethyl acetate in toluene)

Sources & evidence

ORD record
ord-d324de1d710f4e8fb58a179eb35a8820
Source dataset
uspto-grants-2004_04
Patent number
US06723720B2

Reaction notes

Loading…