Butylamine → 2-Butylamino-4-chloro-5-methylsulfonylbenzoic acid

HRID 1606600Notes

Reaction equation

HRID 1606600 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:16]([NH2:20])[CH2:17][CH2:18][CH3:19]>CCOCCO>[CH2:16]([NH:20][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 2210136551521-75-6

Product 1

HCID 215439782-Butylamino-4-chloro-5-methylsulfonylbenzoic acidYield 34%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 2,4-dichloro-5-methylsulfonylbenzoic acid (6.0 g.; 0.0224 mole), butylamine (9 ml.) and ethyl cellosolve (20 ml.) is heated at reflux in a nitrogen atmosphere for 5 hours. The solvent is distilled at reduced pressure and the residue is dissolved in water (75 ml.) then treated with dilute hydrochloric acid which causes the product to precipitate. After recrystallization from butyl chloride there is collected 2.3 g. (34% yield) of 2-butylamino-4-chloro-5-methylsulfonylbenzoic acid, m.p. 187°-9° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux in a nitrogen atmosphere for 5 hours
  3. distillationThe solvent is distilled at reduced pressure
  4. dissolutionthe residue is dissolved in water (75 ml.)
  5. additionthen treated with dilute hydrochloric acid which
  6. customto precipitate
  7. customAfter recrystallization from butyl chloride
  8. customthere is collected 2.3 g

Sources & evidence

ORD record
ord-a1d6f3fcb4104a4ebf5e99b9250a2aab
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

Loading…