Hydrogen Peroxide → 2-Chloro-6-fluorobenzamide

HRID 2269657Notes

Reaction equation

HRID 2269657 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].NC(N)=[O:13].OO.C(=O)([O-])[O-].[K+].[K+]>C(=O)([O-])[O-].[K+].[K+].CC(C)=O.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]([NH2:5])=[O:13]

Participants

8

Reactant 4

HCID 784Hydrogen Peroxide3×HCID 1176Urea3×HCID 11430Potassium CarbonateHCID 695872-Chloro-6-fluorobenzonitrile

Product 1

HCID 985642-Chloro-6-fluorobenzamideYield 97.5%

Reagents, catalysts & solvents 3

HCID 11430Potassium CarbonateCatalyst2×HCID 180AcetoneSolvent3×HCID 962WaterSolvent

Procedure

The procedure of R. Balicki and L. Kaczmarek, Syn. Comm., 23, 3149 (1993)was used. Into a 1 L round bottom flask equipped with a magnetic stirrer was added acetone (60 mL), water (60 mL) , 2-chloro-6-fluorobenzonitrile (14.5 g, 93.5 mmol), urea (22.5 g, 374 mmol), 30% hydrogen peroxide (42.4 g, 374 mmol), and potassium carbonate (1.3 g, 9.0 mmol). The resulting slurry was stirred at room temperature overnight. Additional portions of urea (11.2 g, 30% hydrogen peroxide (41 g), acetone (30 mL) and potassium carbonate (0.63 g) were added and the mixture was allowed to stir for an additional 2 hr. Additional portions of urea (11.2 g, 30% hydrogen peroxide (41 g), acetone (30 mL) and potassium carbonate (0.63 g) were again added and the mixture was allowed to stir overnight. The acetone was removed in vacuo, the residue extracted with methylene chloride, the organics were combined, washed with brine, dried (MgSO4) and the solvent removed in vacuo to give 15.8 g (97.5% yield) of 2-chloro-6-fluorobenzamide (97% pure by GC): mp140-141° C.; 1H NMR (CDCl3) d 7.2-7.4 (m, 2H), 7.0 (m, 1H), 6.3 (s, b, 1H), 5.9 (s, b, 1H).

Workup

  1. customInto a 1 L round bottom flask equipped with a magnetic stirrer
  2. stirringto stir for an additional 2 hr
  3. stirringto stir overnight
  4. customThe acetone was removed in vacuo
  5. extractionthe residue extracted with methylene chloride
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0190e24408bb4ac8a196fe958ad496f7
Source dataset
uspto-grants-2001_12
Patent number
US06329528B1

Reaction notes

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