Hydrochloric Acid → 4-[N'-(2-ethoxycarbonyl-1-acetyl ethylidene)hydrazino]benzene sulfonamide

HRID 650230Notes

Reaction equation

HRID 650230 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[N:13]([O-])=O.[Na+].[CH2:17]([O:19][C:20](=[O:29])[CH2:21][CH:22](C(=O)C)[C:23](=[O:25])[CH3:24])[CH3:18]>C(O)C.O.C(O)C.N1C=CC=CC=1.O>[CH2:17]([O:19][C:20]([CH2:21][C:22](=[N:13][NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:9])=[O:10])=[CH:4][CH:3]=1)[C:23](=[O:25])[CH3:24])=[O:29])[CH3:18]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 5333SulfanilamideHCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 23668193Sodium Nitrite

Product 1

HCID 882324324-[N'-(2-ethoxycarbonyl-1-acetyl ethylidene)hydrazino]benzene sulfonamide

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolventHCID 19096565Water ethanolSolvent

Procedure

To a suspension of 10 g. (58.1 mmoles) of 4-aminobenzenesulfonamide in 50 ml of 1:1 ethanol/water was added 7.3 ml. of concentrated hydrochloric acid. To the cooled mixture was added in portions 4.41. g (63.9 mmoles) of sodium nitrite in 5 ml. of water. The mixture was allowed to come to room temperature and after 15 minutes was poured into a solution of 11.9 g. (63.9 mmoles) of ethyl-3-acetyl-4-oxopentanoate in 12.2 ml. of pyridine, in 25 ml. of ethanol. An orange solid began to separate which was collected after 30 minutes by filtration. After drying, 24.3 g. of material was obtained.

Workup

  1. additionTo a suspension of 10 g
  2. additionTo the cooled mixture was added in portions 4.41
  3. additionwas poured into a solution of 11.9 g
  4. customto separate which
  5. filtrationwas collected after 30 minutes by filtration
  6. customAfter drying
  7. customof material was obtained

Sources & evidence

ORD record
ord-85deb675921d4270852207310957f9af
Source dataset
uspto-grants-2001_08
Patent number
US06271373B1

Reaction notes

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