Hydrochloric Acid → Benzoic acid,3-amino-5-(aminosulfonyl)-4-(3-chlorophenoxy)-

HRID 918609Notes

Reaction equation

HRID 918609 reaction equation
[Cl-].[NH4+].Cl.[Cl:4][C:5]1[CH:6]=[C:7]([CH:25]=[CH:26][CH:27]=1)[O:8][C:9]1[C:17]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[N+:22]([O-])=O.[OH-].[Na+]>[Fe].O>[NH2:22][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([S:18](=[O:20])(=[O:21])[NH2:19])[C:9]=1[O:8][C:7]1[CH:25]=[CH:26][CH:27]=[C:5]([Cl:4])[CH:6]=1)[C:13]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 215060844-(m-Chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid

Product 1

HCID 21506064Benzoic acid,3-amino-5-(aminosulfonyl)-4-(3-chlorophenoxy)-

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of ammonium chloride (1.2 g), metallic iron powder (11 g), concentrated hydrochloric acid (0.05 ml), and water (30 ml) was heated on a steam bath. 4-(m-Chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid (3 g) was added while stirring, and the heating was continued for 6 hours. Then 1N sodium hydroxide (50 ml) was added, and the reaction mixture was filtered. The filter cake was washed twice with 1N sodium hydroxide (50 ml each time). The combined filtrates were adjusted to a pH of 2.5 by the addition of 4N hydrochloric acid. After cooling, the precipitated 3-amino-4-(m-chlorophenoxy)-5-sulphamyl-benzoic acid was collected by suction, and recrystallized from aqueous ethanol. The melting point was 239°-240°C.

Workup

  1. temperaturewas heated on a steam bath
  2. filtrationthe reaction mixture was filtered
  3. washThe filter cake was washed twice with 1N sodium hydroxide (50 ml each time)
  4. additionThe combined filtrates were adjusted to a pH of 2.5 by the addition of 4N hydrochloric acid
  5. temperatureAfter cooling
  6. customthe precipitated 3-amino-4-(m-chlorophenoxy)-5-sulphamyl-benzoic acid was collected by suction
  7. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-c78fdadb0c204efebd9aa6699766b8c3
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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