Diethylamine → Benzoic Acid

HRID 1586181Notes

Reaction equation

HRID 1586181 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8](S(F)(=O)=O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(NCC)C>ClCCCl>[C:4]([OH:6])(=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 888732-Chloro-5-(fluorosulpho)benzoic acid

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-chloro-5-(fluorosulfonyl)benzoic acid (11.93 g, 0.05 mol), diethylamine (10.97 g, 0.15 mol) and 1,2-dichloroethane (100 ml) is refluxed for 8 hours. The reaction mixture is evaporated, and the residue is dissolved in ethyl acetate. A solid is collected by filtration, and the filtrate is evaporated to dryness to afford 15.5 g of 2-chloro-5-diethylaminosulfonyl)benzoic acid.

Workup

  1. temperatureis refluxed for 8 hours
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. filtrationA solid is collected by filtration
  5. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-2a4121e7618446e98f1cfa946b34a21e
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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