Dimethylformamide → Benzoic acid, 2-[[[(4-fluorophenyl)amino]acetyl]amino]-

HRID 1490314Notes

Reaction equation

HRID 1490314 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])=[O:4].[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.CN(C=O)C.[OH-].[K+]>O>[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][CH2:2][C:3]([NH:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=[O:9])=[O:4])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97314-FluoroanilineHCID 14797Potassium HydroxideHCID 10611190HCID 10611190, compound

Product 1

HCID 10493569Benzoic acid, 2-[[[(4-fluorophenyl)amino]acetyl]amino]-Yield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(N-bromoacetylamino)benzoic acid from Example 79 (8.00 g, 31.0 mmol), para-fluoroaniline (7.34 mL, 77.5 mmol) and DMF (80 mL) was heated to 75° C. for 8 h. The mixture was cooled, poured over H2O (1 L) and 5% KOH (300 mL) and washed with CH2Cl2 (3×300 mL). The aqueous layer was acidified to pH 2 with 2N HCl, cooled below room temperature and filtered. The filter cake was rinsed with water (60 mL) and dried under high vacuum at 45° C. to yield 7.98 g (89%) of the title compound as an off-white solid; 1H NMR (DMSO-d6) δ 13.45 (broad s, 1H), 12.00 (s, 1H), 8.72 (d, J=8, 1H), 7.94 (dd, J=8, J=1.2, 1H), 7.59 (td, J=7.2, J=1.6, 1H), 7.13 (td, J=7.2, J=0.8, 1H), 6.95 (m, 2H), 6.58 (m, 2H), 6.47 (s, 1H), 3.82 (s, 2H); 13C NMR (DMSO-d6) δ 170.73, 169.04, 154.95 (J=232.0), 144.78, 140.54, 134.15, 131.13, 122.69, 119.43, 116.00, 115.38 (J=21.9), 113.22 (J=7.6), 49.31.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with CH2Cl2 (3×300 mL)
  3. temperaturecooled below room temperature
  4. filtrationfiltered
  5. washThe filter cake was rinsed with water (60 mL)
  6. customdried under high vacuum at 45° C.

Sources & evidence

ORD record
ord-6037aed2da414f63980be516b5b3695e
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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