Potassium Carbonate → 2-Cyano-2-fluoromethoxyiminoacetamide

HRID 965413Notes

Reaction equation

HRID 965413 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9](=[N:13][OH:14])[C:10]([NH2:12])=[O:11])#[N:8].[F:15][CH2:16]Br>CS(C)=O.CN(C)C=O>[C:7]([C:9](=[N:13][O:14][CH2:16][F:15])[C:10]([NH2:12])=[O:11])#[N:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 61108BromofluoromethaneHCID 67624432-Cyano-2-hydroxyiminoacetamide

Product 1

HCID 540352372-Cyano-2-fluoromethoxyiminoacetamideYield 72.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (85.7 g, 0.62 mol) was added to 2-cyano-2-hydroxyiminoacetamide (35.0 g, 0.31 mol) in dimethylsulfoxide (150 ml) under ice-cooling, and the mixture was stirred for 20 mins. On the other hand, a solution of fluoromethyl bromide (27.8 g, 0.31 mol) in dimethylformamide (27 ml) was added dropwise to the reaction mixture under ice-cooling, and the resultant mixture was stirred at a room temperature for 1.5 hrs. The mixture was dispersed in ice water (1 kg), and it was extracted three times with ethyl acetate (500 ml, 400 ml, and 300 ml, respectively). The combined extracts were washed twice with saturated brine (150 ml) and dried over magnesium sulfate (100 g). The ethyl acetate was distilled off under reduced pressure until the residue weighed 65.5 g. The residue was cooled, filtered, and dried to give 2-cyano-2-fluoromethoxyimino-acetamide (32.8 g, yield: 72.6%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionit was extracted three times with ethyl acetate (500 ml, 400 ml, and 300 ml
  4. washThe combined extracts were washed twice with saturated brine (150 ml)
  5. dry with materialdried over magnesium sulfate (100 g)
  6. distillationThe ethyl acetate was distilled off under reduced pressure until the residue
  7. temperatureThe residue was cooled
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-603b9bf1ee6d4252bccdcb11098269ad
Source dataset
uspto-grants-1998_06
Patent number
US05773624

Reaction notes

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