Acetic Anhydride → HCID 15790822, compound

HRID 357538Notes

Reaction equation

HRID 357538 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[Cl:8][C:9]1[C:10]([N:19]2C(C=O)=[C:22]([C:26]#[N:27])[CH:21]=[N:20]2)=[N:11][N:12]([CH3:18])[C:13]=1[O:14][CH:15]([F:17])[F:16].[C:28]([O-])(=[O:30])[CH3:29].[Na+]>B(F)(F)F.CCOCC.C(OCC)(=O)C>[Cl:8][C:9]1[C:10]([N:19]2[C:2]([CH:1]([O:3][C:28](=[O:30])[CH3:29])[O:4][C:5](=[O:7])[CH3:6])=[C:22]([C:26]#[N:27])[CH:21]=[N:20]2)=[N:11][N:12]([CH3:18])[C:13]=1[O:14][CH:15]([F:17])[F:16]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 15790818HCID 15790818, compound

Product 1

HCID 15790822HCID 15790822, compound

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5 ml acetic anhydride is cooled to 0°-5° C. and 2 drops boron trifluoride-etherate are added. Then 2.3 g (7.6 mmol) 1-(4-chlor-5-difluormethoxy-1-methyl-3-pyrazolyl)-5-formyl-4-pyrazol-carbonitrile is slowly added dropwise and stirring is continued for another 1.5 hours at room temperature. 9 ml of 10% sodium acetate solution is added, stirring is continued for 20 minutes at room temperature and then the mixture is shaken up with ethyl acetate. The combined ethyl acetate phases are washed with a solution of sodium hydrogen carbonate and sodium chloride, dried and concentrated. Purification is by column chromatography using a hexane/ethyl acetate mixture.

Workup

  1. stirringstirring
  2. waitis continued for 20 minutes at room temperature
  3. washThe combined ethyl acetate phases are washed with a solution of sodium hydrogen carbonate and sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-e016dc10801442e68f9581aba2314bb9
Source dataset
uspto-grants-1998_11
Patent number
US05840912

Reaction notes

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