Potassium Carbonate → HCID 53831628, compound

HRID 965409Notes

Reaction equation

HRID 965409 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][N:8]=[C:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[F:17][CH2:18]Br>CS(C)=O.CN(C)C=O>[F:17][CH2:18][O:7][N:8]=[C:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 61108BromofluoromethaneHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 53831628HCID 53831628, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (110.6 g, 0.8 ml) was added to ethyl 2-hydroxyimino-cyanoacetate (56.8 g, 0.4 mol) in dimethylsulfoxide (200 ml) under ice-cooling, and the mixture was stirred for 10 mins, and then Fluoromethyl bromide (48.8 g, 0.4 mol) in N,N-dimethylformamide (40 ml) was added dropwise to the mixture under ice-cooling. The mixture was stirred at an internal temperature of 20° to 30° C. for 2.5 hrs. The reaction solution was dispersed in ice water (1 L), and it was extracted with ethyl acetate (800 ml, 500 ml, and 500 ml). The combined extracts were washed twice with saturated brine (300 ml) and dried over sodium sulfate, and then concentrated to give a concentrate (66.4 g) which was purified by column chromatography using silica gel (60 g) to give ethyl 2-fluoromethoxyimino-cyanoacetate (46.6 g, yield: 66.9%) as an oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe mixture was stirred at an internal temperature of 20° to 30° C. for 2.5 hrs
  4. extractionit was extracted with ethyl acetate (800 ml, 500 ml, and 500 ml)
  5. washThe combined extracts were washed twice with saturated brine (300 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give
  9. concentrationa concentrate (66.4 g) which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7f06742ff1e444a0af604c39de35a5c7
Source dataset
uspto-grants-1998_06
Patent number
US05773624

Reaction notes

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