Dimethylformamide → HCID 18950416, compound

HRID 248837Notes

Reaction equation

HRID 248837 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].C[N:17]([CH3:20])[CH:18]=O>>[CH3:6][C:3]1[C:4]2[N:5]=[CH:18][N:17]([C:2]3[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=3[C:4]#[N:5])[C:20]=2[CH:8]=[CH:9][CH:2]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Product 1

HCID 18950416HCID 18950416, compoundYield 68%

Conditions

Temperature
80 °C

Procedure

The title A compound (133 mg, 1.01 mmol), 2-fluorbenzonitrile (164 μL, 1.51 mmol) and finely ground potassium carbonate (279 mg, 2.02 mmol) were combined in 1 mL of N,N-dimethylformamide (DMF) and heated to 80° C. After stirring for 20 hours, the DMF was removed in vacuo and the brown solid residue was partitioned between saturated sodium bicarbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were dried over magnesium sulfate, filtered and the solvent removed. The residue was purified by flash chromatography (20 g silica gel, eluted with 50% ethyl acetate, hexane) to provide 160 mg (68%) of a white solid.

Workup

  1. customthe DMF was removed in vacuo
  2. customthe brown solid residue was partitioned between saturated sodium bicarbonate and ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe residue was purified by flash chromatography (20 g silica gel, eluted with 50% ethyl acetate, hexane)

Sources & evidence

ORD record
ord-5196b29a0ca342eea5fa9f94937114db
Source dataset
uspto-grants-1993_05
Patent number
US05212177

Reaction notes

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