Hydrochloric Acid → N1-hexanoylsulfanilamide

HRID 861187Notes

Reaction equation

HRID 861187 reaction equation
C([NH:4][C:5]1[CH:21]=[CH:20][C:8]([S:9]([NH:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].Cl>O>[C:13]([NH:12][S:9](=[O:10])([C:8]1[CH:7]=[CH:6][C:5]([NH2:4])=[CH:21][CH:20]=1)=[O:11])(=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54008860HCID 54008860, compound

Product 1

HCID 14338356N1-hexanoylsulfanilamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N4 -acetyl-N1 -hexanoylsulfanilamide from the previous step was treated with sodium hydroxide (24.6 g) in D.I. water (200 mL) while heating to reflux. After 3 hours reaction time, the heating was stopped and the solution pH adjusted to 8 with 2N HCl. The solution was cooled in an ice bath and then filtered to remove sulfanilamide. The filtrate was acidified with aqueous HCl to pH 2 to precipitate the product, N1 -hexanoylsulfanilamide, 37.9 g. This material was recrystallized from hot ethanol (75 mL) and precipitated by addition of 40 mL D.I. water to afford recrystallized N1 -hexanoylsulfanilamide, 24.8 g (43% overall yield). H1 -NMR indicated a purity >90%.

Workup

  1. customAfter 3 hours reaction time
  2. temperatureThe solution was cooled in an ice bath
  3. filtrationfiltered
  4. customto remove sulfanilamide
  5. customto precipitate the product, N1 -hexanoylsulfanilamide, 37.9 g
  6. customThis material was recrystallized from hot ethanol (75 mL)
  7. customprecipitated by addition of 40 mL D.I
  8. customwater to afford
  9. customrecrystallized

Sources & evidence

ORD record
ord-a9daf775c772421e8d6e5d04f87cea63
Source dataset
uspto-grants-1998_02
Patent number
US05713988

Reaction notes

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