Carbon Dioxide → HCID 57733334, compound

HRID 1962404Notes

Reaction equation

HRID 1962404 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[F:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14](F)[C:11]=1[C:12]#[N:13].C(=O)([O-])[O-].[K+].[K+].Cl.C(=O)=O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:8])[CH:5]([C:6]#[N:7])[C:14]1[CH:15]=[CH:16][CH:17]=[C:10]([F:9])[C:11]=1[C:12]#[N:13])[CH3:2]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 57733334HCID 57733334, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of cyanoacetic acid ethyl ester (26.7 mL, 251 mmol), 2,6-difluorobenzonitrile (33.2 g, 239 mmol) and potassium carbonate (82.5 g, 597 mmol) in dimethyl sulfoxide (120 mL) was stirred at +55° C. for 16 hours and poured into ice-water mixture (ca. 400 mL). It was acidified with conc. aq. HCl with caution (CO2 evolution) and extracted with ethyl acetate (600 ml). The organic phase was washed with brine (100 mL) and evaporated to give 55.1 g of a pale yellow solid that was used in the next step without further purification. 1H NMR (500 MHz, CDCl3): 1.35 (t, J=7.0 Hz, 3H), 4.34 (m, 2H), 5.13 (s, 1H), 7.33 (t, J=8.4 Hz, 1H), 7.57 (d, J=7.9 Hz, 1H), 7.33 (dd, J=7.9 Hz, J=13.9 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate (600 ml)
  2. washThe organic phase was washed with brine (100 mL)
  3. customevaporated

Sources & evidence

ORD record
ord-5d08a9ec7d5340589d65da1e4fe94770
Source dataset
uspto-grants-2013_04
Patent number
US08415373B2

Reaction notes

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