4-Fluorobenzoyl chloride → N-(3-Cyano-4,5-dihydro-2-furanyl)-4-fluorobenzamide

HRID 714776Notes

Reaction equation

HRID 714776 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][CH2:5][C:6]=1[C:7]#[N:8].[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1>N1C=CC=CC=1>[C:7]([C:6]1[CH2:5][CH2:4][O:3][C:2]=1[NH:1][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][C:10]([F:9])=[CH:11][CH:12]=1)#[N:8]

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 134169562-Amino-4,5-dihydrofuran-3-carbonitrile

Product 1

HCID 7655792N-(3-Cyano-4,5-dihydro-2-furanyl)-4-fluorobenzamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-4,5-dihydrofuran-3-carbonitrile (3.5 g) obtained in Step D in pyridine (8 mL) was added dropwise 4-fluorobenzoyl chloride (5.5 g) in an ice bath, and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, and to the residue was added dropwise saturated aqueous sodium hydrogen carbonate solution in an ice bath. The resulting solid was collected by filtration, and washed with water to give the title compound (7.1 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionto the residue was added dropwise saturated aqueous sodium hydrogen carbonate solution in an ice bath
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-a73523436d094cb5be35d0ab2d8526b0
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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