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Sulfuric Acid → HCID 21506021, compound

HRID 918687
Notes
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Reaction equation

HRID 918687 reaction equation
NC1C=C(C=C(S(=O)(=O)N)C=1NC1C=CC=CC=1)C(O)=O.OS(O)(=O)=O.[NH:27]([C:34]1[C:46]([S:47](=[O:50])(=[O:49])[NH2:48])=[CH:45][C:37]([C:38]([O:40]CCCC)=[O:39])=[CH:36][C:35]=1[NH:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH-].[Na+]>O.C(O)CCC>[NH:27]([C:34]1[C:46]([S:47](=[O:50])(=[O:49])[NH2:48])=[CH:45][C:37]([C:38]([OH:40])=[O:39])=[CH:36][C:35]=1[NH:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21505992HCID 21505992, compoundHCID 21506098HCID 21506098, compound

Product 1

HCID 21506021HCID 21506021, compound

Reagents, catalysts & solvents 2

HCID 2631-Butanol
Solvent
HCID 962WaterSolvent

Procedure

A mixture of 3-amino-4-anilino-5-sulphamyl-benzoic acid (4 g), n-butanol (50 ml), and conc. H2SO4 (0.4 ml) was boiled under reflux with water separator for 5 days. The resulting solution of butyl 4-anilino-3-butylamino-5-sulphamyl-benzoate was saponified by addition of 2N sodium hydroxide and boiling under reflux for 45 minutes. After neutralization with 4N hydrochloric acid, the reaction mixture was evaporated in vacuo. The residue was dissolved in hot water (50 ml), and the 4-anilino-3-butylamino-5-sulphamyl-benzoic acid was precipitated by addition of 4N hydrochloric acid to pH 3. The crude acid was dissolved in diethyl ether (50 ml), and undissolved impurities were filtered off. The etherial solution was evaporated to dryness, and the residue was recrystallized from acetone-water and aqueous ethanol, after which the compound was obtained with a melting point of 230-231°C.

Workup

  1. temperatureunder reflux for 45 minutes
  2. customAfter neutralization with 4N hydrochloric acid, the reaction mixture was evaporated in vacuo
  3. dissolutionThe residue was dissolved in hot water (50 ml)
  4. customthe 4-anilino-3-butylamino-5-sulphamyl-benzoic acid was precipitated by addition of 4N hydrochloric acid to pH 3
  5. dissolutionThe crude acid was dissolved in diethyl ether (50 ml)
  6. filtrationundissolved impurities were filtered off
  7. customThe etherial solution was evaporated to dryness
  8. customthe residue was recrystallized from acetone-water and aqueous ethanol
  9. customafter which the compound was obtained with a melting point of 230-231°C.

Sources & evidence

ORD record
ord-5c28b90ea50a4b2baaa687c4b56dead6
Source dataset
uspto-grants-1976_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03971819

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes