Sodium → HCID 21506153, compound

HRID 918641Notes

Reaction equation

HRID 918641 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:22](=[O:25])(=[O:24])[NH2:23])[C:12]=1[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:7]([OH:9])=[O:8])([O-])=O.[H][H].[Na]>O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:22](=[O:24])(=[O:25])[NH2:23])[C:12]=1[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])=[O:15])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 21506068HCID 21506068, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21506153HCID 21506153, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 3-nitro-4-phenylsulphonyl-5-sulphamyl-benzoic acid (6 g) in water (300 ml) was hydrogenated at room temperature and 1.1 atmospheres hydrogen pressure after addition of Pd-on-carbon catalyst (0.3 g catalyst containing 10% Pd). After the hydrogen uptake had become negligible, the reaction mixture was neutralized by addition of 2N sodium hydroxde, and the catalyst was removed from the resulting suspension by filtration. The filtrate was adjusted to a pH of 2.5 by addition of 4N hydrochloric acid, and the precipitated 3-amino-4-phenylsulphonyl-5-sulphamyl-benzoic acid was collected by suction. After recrystallization from aqueous ethanol, the acid had a melting point of 278°C (decomp.).

Workup

  1. customwas hydrogenated at room temperature
  2. customthe catalyst was removed from the resulting suspension by filtration
  3. additionThe filtrate was adjusted to a pH of 2.5 by addition of 4N hydrochloric acid
  4. customthe precipitated 3-amino-4-phenylsulphonyl-5-sulphamyl-benzoic acid was collected by suction
  5. customAfter recrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-1e0553e42a7348cea9b6c42dd85967a8
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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