Dimethylformamide → Benzamide

HRID 56071Notes

Reaction equation

HRID 56071 reaction equation
C[N:2]([CH:4]=[O:5])C.F[C:7]1[CH:8]=[C:9]([CH:12]=[C:13](C#CC2C=CC=CN=2)[CH:14]=1)C#N>C(=O)(O)[O-].C([N+](CC)(CC)CC)C.C(Cl)Cl>[C:4]([NH2:2])(=[O:5])[C:7]1[CH:8]=[CH:9][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 462082493-Fluoro-5-((pyridin-2-yl)ethynyl)benzonitrile

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 2

HCID 11805541Tetraethylammonium bicarbonateCatalystHCID 6344DichloromethaneSolvent

Procedure

A DMF (1 mL) solution of 3-fluoro-5-(pyridin-2-ylethynyl)benzonitrile (50 mg, 0.22 mmol) and tetraethylammonium bicarbonate (0.44 mmol) was heated at 120° C. for 10 min. The yellow reaction mixture was cooled and diluted with DCM (10 mL) and washed with aqueous LiCl (5% w/v, 3×5 mL), water (3×5 mL), brine and dried over anhydrous MgSO4. Removal of DCM under reduced pressure yielded quantitative benzamide as a white solid; mp 175-176° C. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): δ 8.63 (d, J=4.9 Hz, 1H), 8.17 (s, 1H), 7.97 (s, 1H), 7.88 (td, J=7.8, 1.7 Hz, 1H), 7.76-1.52 (m, 4H), 7.44 (m, 1H) ppm 13C-NMR (75 MHz, DMSO-d6) δ (ppm): 166.0, 162.0 (d, JCF=246.6 Hz), 150.78, 142.17, 137.68 (d, JCF=8.0 Hz), 137.41, 128.06, 127.47, 124.45, 123.85 (d, JCF=9.1 Hz), 121.34 (d, JCF=22.7 Hz), 116.17 (d, JCF=22.7 Hz), 90.56, 86.83 ppm HRMS (m/z): [M+H]+ calc. for C14H10F2O, 241.0772. found 241.0783.

Workup

  1. temperatureThe yellow reaction mixture was cooled
  2. washwashed with aqueous LiCl (5% w/v, 3×5 mL), water (3×5 mL), brine
  3. dry with materialdried over anhydrous MgSO4
  4. customRemoval of DCM under reduced pressure

Sources & evidence

ORD record
ord-87212d871e874fed9fd936e1e5f3545d
Source dataset
uspto-grants-2016_09
Patent number
US09434699B2

Reaction notes

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