Sodium Hydroxide → HCID 54145842, compound

HRID 1730432Notes

Reaction equation

HRID 1730432 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]([S:21](=[O:28])(=[O:27])[NH:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]([S:21](=[O:28])(=[O:27])[NH:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 54126433HCID 54126433, compound

Product 1

HCID 54145842HCID 54145842, compound

Procedure

The mixture of 5.1 g of 4-(4-acetamidophenylmercapto)-3-n-butylamino-5-n-butylsulfamoyl benzoic acid and 75 ml of 2N aqueous sodium hydroxide is refluxed for 2 hours under nitrogen and filtered after cooling to room temperature. The filtrate is acidified with glacial acetic acid to pH=4, the precipitate filtered off and recrystallized several times from aqueous ethanol. It is dissolved in the minimum amount of 2N aqueous sodium hydroxide, chromatographed on silica gel and the column eluted with ethyl acetate-methanol-saturated aqueous amonia (65: 25: 10), to yield the 4-(4-amino-phenylmercapto)-3-n-butylamino-5-n-butylsulfamoylbenzoic acid of the formula ##SPC17##

Workup

  1. temperatureis refluxed for 2 hours under nitrogen
  2. filtrationfiltered
  3. filtrationthe precipitate filtered off
  4. customrecrystallized several times from aqueous ethanol
  5. dissolutionIt is dissolved in the minimum amount of 2N aqueous sodium hydroxide
  6. customchromatographed on silica gel
  7. washthe column eluted with ethyl acetate-methanol-saturated aqueous amonia (65: 25: 10)

Sources & evidence

ORD record
ord-f781a1b9a8bd43a1b071503e74ade988
Source dataset
uspto-grants-1976_11
Patent number
US03992440

Reaction notes

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