Butanal → 4-[(4-Aminophenyl)sulfanyl]-3-(butylamino)-5-sulfamoylbenzoic acid

HRID 1576731Notes

Reaction equation

HRID 1576731 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH2:25])=[CH:7][CH:6]=1)(=O)C.[CH:26](=O)[CH2:27][CH2:28][CH3:29].C([BH3-])#N.[Na+].Cl>CN(C)C=O.O>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([S:11][C:12]2[C:20]([S:21](=[O:23])(=[O:24])[NH2:22])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 261ButanalHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 54216006HCID 54216006, compound

Product 1

HCID 542886564-[(4-Aminophenyl)sulfanyl]-3-(butylamino)-5-sulfamoylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To the solution of 1.52 g of 4-(4-acetamidophenylmercapto)-3-amino-5-sulfamoylbenzoic acid in 600 ml of dimethylformamide, 40 g of butyraldehyde and 1.60 g of molecular sieves [Na12 (AlSiO4)12. 27 H2O], 36 g of sodium cyanoborohydride are added while stirring under nitrogen and keeping the temperature between about 20° and 30° for 1 hour. After stirring the mixture for 68 hours at room temperature, 6 lt of water are added, followed by 110 ml of concentrated hydrochloric acid and stirring is continued for 1 hour. The precipitate formed is filtered off, washed with water, dissolved in 1.2 lt of 2N aqueous sodium hydroxide and the solution refluxed for 2 hours under nitrogen. After cooling to room temperature it is filtered and the filtrate combined with 250 ml of glacial acetic acid. The precipitate formed is collected, 333 g thereof are dissolved in 2.8 lt of hot, 80% aqueous acetonitrile, the solution filtered, the filter washed with 500 ml more of said acetonitrile and the filtrate diluted with 3.3 lt of hot water. The precipitate formed at 14° is filtered off, taken up in 2.15 lt of hot, 90% aqueous ethanol and the solution diluted with 2.5 lt of hot water. The solids separated after cooling are collected and washed with water, to yield the 4-(4-aminophenylmercapto)-3-n-butylamino-5-sulfamoylbenzoic acid melting at 232°-234°, it is identical with that obtained according to Example 3.

Workup

  1. customthe temperature between about 20° and 30°
  2. customfor 1 hour
  3. stirringAfter stirring the mixture for 68 hours at room temperature
  4. stirringstirring
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washwashed with water
  8. dissolutiondissolved in 1.2 lt of 2N aqueous sodium hydroxide
  9. temperaturethe solution refluxed for 2 hours under nitrogen
  10. filtrationis filtered
  11. customThe precipitate formed
  12. customis collected
  13. dissolution333 g thereof are dissolved in 2.8 lt of hot, 80% aqueous acetonitrile
  14. filtrationthe solution filtered
  15. washthe filter washed with 500 ml more of said acetonitrile
  16. additionthe filtrate diluted with 3.3 lt of hot water
  17. customThe precipitate formed at 14°
  18. filtrationis filtered off
  19. additionthe solution diluted with 2.5 lt of hot water
  20. customThe solids separated
  21. temperatureafter cooling
  22. customare collected
  23. washwashed with water

Sources & evidence

ORD record
ord-c1432d07300e48d5ae2e3876602d7f35
Source dataset
uspto-grants-1976_09
Patent number
US03982018

Reaction notes

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