Water → 2-Difluoromethoxy-6-fluorobenzamide O-cyclopropylmethyl oxime

HRID 1840659Notes

Reaction equation

HRID 1840659 reaction equation
[H-].[Na+].[F:3][CH:4]([F:17])[O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:7]=1[C:8](=[N:10][OH:11])[NH2:9].Br[CH2:19][CH:20]1[CH2:22][CH2:21]1.O>CN(C)C=O>[CH:20]1([CH2:19][O:11][N:10]=[C:8]([NH2:9])[C:7]2[C:12]([F:16])=[CH:13][CH:14]=[CH:15][C:6]=2[O:5][CH:4]([F:3])[F:17])[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 545406342-Difluoromethoxy-6-fluorobenzamidoxime

Product 1

HCID 867583662-Difluoromethoxy-6-fluorobenzamide O-cyclopropylmethyl oximeYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.4 g of 80% pure sodium hydride was added to a solution of 3.0 g of 2-difluoromethoxy-6-fluorobenzamidoxime in 30 ml of dimethylformamide (DMF) at 0 to 5° C. and the mixture was stirred at this temperature for 3 hours. 1.8 g of bromocyclopropylmethane were subsequently added at the same temperature, and stirring was subsequently continued for 2 hours at 5° C. and overnight at room temperature. The batch was stirred into 300 ml of water and extracted three times with in each case 70 ml of cyclohexane. After the cyclohexane had been evaporated, 1.9 g of the desired product were obtained.

Workup

  1. stirringstirring
  2. waitwas subsequently continued for 2 hours at 5° C. and overnight at room temperature
  3. extractionextracted three times with in each case 70 ml of cyclohexane
  4. customAfter the cyclohexane had been evaporated

Sources & evidence

ORD record
ord-e78294ea5fc14d3e9451f7cff9e47245
Source dataset
uspto-grants-2004_01
Patent number
US06680402B2

Reaction notes

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