Dimethylacetamide → HCID 19365948, compound

HRID 850099Notes

Reaction equation

HRID 850099 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=1)=[O:11].[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1.[Na].CN(C)C(=O)C>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)=[CH:14][CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 19365975HCID 19365975, compoundHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 19365948HCID 19365948, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(2,4-difluorophenyl)-1-(4-fluorophenyl)-1-ethanone (5.0 g, 20 mmol-see EP-A-0069442), sodium 1,2,4-triazole (2.18 g, 24 mmol) and N,N-dimethylacetamide (100 ml) was stirred at 100° C. for 18 hours. The mixture was diluted with xylene (300 ml) and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (500 ml) and washed with water (3×50 ml). The organic solution was dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (eluting with ethyl acetate:dichloromethane 1:1) gave a white solid (1.05 g, 18%), which was characterised by 1H-N.M.R. spectroscopy.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (500 ml)
  3. washwashed with water (3×50 ml)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification
  7. washby flash chromatography (eluting with ethyl acetate:dichloromethane 1:1)

Sources & evidence

ORD record
ord-bf8e9fe2409d4b3b9f25450dfecb8d7a
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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