Nicotinic acid, hydrazide → HCID 86757853, compound

HRID 277112

Reaction equation

HRID 277112 reaction equation
Cl.C(O[C:5](=[NH:16])[CH2:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8])C.[OH-].[Na+].C(=O)(O)[O-].[Na+].[C:24]([NH:32][NH2:33])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=1>C(Cl)(Cl)Cl.O1CCOCC1>[NH2:16][C:5](=[N:33][NH:32][C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=1)[CH2:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

7

Reactant 4

HCID 11112Nicotinic acid, hydrazideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 700894412-(Phenylsulfonyl)-ethanimidic acid ethyl ester hydrochloride

Product 1

HCID 86757853HCID 86757853, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 23.6 g (0.089 mol) 2-(phenylsulfonyl)-ethanimidic acid ethyl ester hydrochloride in 300 ml chloroform was treated with 98 ml 1N aqueous sodium hydoxide. 200 ml of a saturated aqueous sodiumbicarbonate solution was added and the mixture was extracted with chloroform. The extracts were combined and dried with sodium sulfate and the solvents were distilled off under reduced pressure. The resulting colorless oil was stirred together with 13.5 g (0.098 mol) nicotinic acid hydrazide in 500 ml dioxane over night at 50° C. The resulting precipitate was filtered off and dried. A yield of 15.5 g (55%) nicotinic acid (1-amino-2-benzenesulfonyl-ethylidene)-hydrazide was obtained as white solid, MS m/e (%): 319 (M+H+, 100).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialdried with sodium sulfate
  3. distillationthe solvents were distilled off under reduced pressure
  4. filtrationThe resulting precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-da3a986cd3924997b9a302428823fde1
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Linked notes

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