Hydrochloric Acid → 3-n-Butylamino-4-chloro-5-methylsulfinylbenzoic acid

HRID 1606622Notes

Reaction equation

HRID 1606622 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:12]([CH3:14])=[O:13])[C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.Cl>C(O)CCC>[CH2:3]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:12]([CH3:14])=[O:13])[C:10]=1[Cl:11])[C:5]([OH:7])=[O:6])[CH2:2][CH2:10][CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 215439723-Amino-4-chloro-5-methylsulfinylbenzoic acid

Product 1

HCID 543482303-n-Butylamino-4-chloro-5-methylsulfinylbenzoic acid

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 3-amino-4-chloro-5-methylsulfinylbenzoic acid (4.67 g.; 0.02 mole) in n-butanol (150 ml.) containing concentrated sulfuric acid (2 ml.) is refluxed for 48 hours in a Soxhlet extractor containing type 4A molecular sieves (100 g.). The solvent is distilled at reduced pressure and the residue is treated with water (50 ml.), 10N sodium hydroxide (20 ml.) and ethanol (20 ml.) and refluxed for 1 hour to hydrolyze any butyl ester which may have formed. The reaction mixture is cooled and acidified with dilute hydrochloric acid to give 3-n-butylamino-4-chloro-5-methylsulfinylbenzoic acid which melts at 158° C. after recrystallization from ethanol and water.

Workup

  1. temperatureis refluxed for 48 hours in a Soxhlet extractor
  2. distillationThe solvent is distilled at reduced pressure
  3. additionthe residue is treated with water (50 ml.), 10N sodium hydroxide (20 ml.) and ethanol (20 ml.)
  4. temperaturerefluxed for 1 hour
  5. custommay have formed
  6. temperatureThe reaction mixture is cooled

Sources & evidence

ORD record
ord-3c790168f9544381a0a9d4da457576ad
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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