Sodium hydride → HCID 54459581, compound

HRID 1586098Notes

Reaction equation

HRID 1586098 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[C:3]=1[C:4](=[N:6][OH:7])[NH2:5].[CH:16]1([CH2:19]Br)[CH2:18][CH2:17]1.[H-].[Na+]>CN(C=O)C>[CH:16]1([CH2:19][O:7][N:6]=[C:4]([NH2:5])[C:3]2[C:8]([C:12]([F:13])([F:14])[F:15])=[CH:9][CH:10]=[CH:11][C:2]=2[F:1])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 3407084HCID 3407084, compound

Product 1

HCID 54459581HCID 54459581, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 100 ml of DMF was dissolved 26.6 g of 2-fluoro-6-trifluoromethylbenzamidoxime and 17.8 g of cyclopropylmethylbromide, and to the solution was added 4.8 g of sodium hydride (60% in oil) at 10° C. over 30 min. The solution was then stirred for 3 hours, and the solution reacted was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography to obtain 24.8 g of the objective compound. m.p. 63-64° C.

Workup

  1. customthe solution reacted
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93241904648f42eb892ff94f936cd9a3
Source dataset
uspto-grants-1999_08
Patent number
US05942538

Reaction notes

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