Sulfuric Acid → 3-Chloro-5-fluorobenzamide

HRID 2372235Notes

Reaction equation

HRID 2372235 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([F:15])[CH:14]=1)[C:10]#[N:11]>O>[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([F:15])[CH:14]=1)[C:10]([NH2:11])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 27348413-Chloro-5-fluorobenzonitrile

Product 1

HCID 37866593-Chloro-5-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of sulfuric acid (500 ml) and water (100 ml) is heated to 95° and 3-chloro-5-fluorobenzonitrile (94.8 gms) added. After 4 hours the mixture is cooled and poured over ice and water added to make 3.6 L. In 1.2 L portions the mixture is filtered, the solid rinsed with hexane and the aqueous rinsed with hexane (4×120 ml) then extracted with ethyl acetate (2×100 ml). The solid and the ethyl acetate extracts were combined, dried over magnesium sulfate and stripped to give 3-chloro-5-fluorobenzamide as a white solid.

Workup

  1. temperatureis heated to 95°
  2. temperatureAfter 4 hours the mixture is cooled
  3. additionadded
  4. filtrationIn 1.2 L portions the mixture is filtered
  5. washthe solid rinsed with hexane
  6. washthe aqueous rinsed with hexane (4×120 ml)
  7. extractionthen extracted with ethyl acetate (2×100 ml)
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-e4348596c4a5496dbb27037155a6f6b0
Source dataset
uspto-grants-1992_03
Patent number
US05098466

Reaction notes

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