Hydrochloric Acid → HCID 17774527, compound

HRID 378300Notes

Reaction equation

HRID 378300 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:16]=[C:17]([N:26](C)[C:27](=O)C)[CH:18]=[C:19]([N:21](C(=O)C)[CH3:22])[CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.[ClH:31]>[OH-].[Na+]>[ClH:31].[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:16]=[C:17]([NH:26][CH3:27])[CH:18]=[C:19]([NH:21][CH3:22])[CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19353552HCID 19353552, compound

Product 1

HCID 17774527HCID 17774527, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.113 g (0.00026 mol) of N-[3-(4-acetylamino-phenylsulfonylamino)-5-(acetyl-methyl-amino)-phenyl]-N-methyl-acetamide was dissolved in 10 ml of 1N NaOH and boiled at reflux for 2 hours. The mixture was neutralized with 1N HCl, extracted with ethyl acetate and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was dissolved in 4 ml of methanol and treated with 3 ml of 2M HCl. After the addition of 7-8 ml of ethyl acetate the product separated out slowly. It was filtered off and dried in a vacuum. There was obtained 0.085 g (74%) of 4-amino-N-(3,5-bis-methylamino-phenyl)-benzenesulfonamide hydrochloride (1:2.6) as a pink coloured amorphous solid. MS (ISN): me/e=305 (C14H17N4O2S-).

Workup

  1. temperatureat reflux for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customAfter removal of the solvent the residue
  5. dissolutionwas dissolved in 4 ml of methanol
  6. additiontreated with 3 ml of 2M HCl
  7. additionAfter the addition of 7-8 ml of ethyl acetate the product
  8. customseparated out slowly
  9. filtrationIt was filtered off
  10. customdried in a vacuum

Sources & evidence

ORD record
ord-8e7e8dbf0e874d989458399db3f83475
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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