(Phenylsulfanyl)acetaldehyde → N-Methyl-4-[2-[2-(phenylthio)ethylidene]hydrazino]benzenemethanesulphonamide

HRID 2248011Notes

Reaction equation

HRID 2248011 reaction equation
[C:1]1([S:7][CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH:12]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][S:21]([NH:24][CH3:25])(=[O:23])=[O:22])=[CH:16][CH:15]=1)[NH2:13]>C(O)C.O>[CH3:25][NH:24][S:21]([CH2:20][C:17]1[CH:18]=[CH:19][C:14]([NH:12][N:13]=[CH:9][CH2:8][S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:15][CH:16]=1)(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 579732(Phenylsulfanyl)acetaldehydeHCID 142342634-Hydrazino-N-methylbenzenemethanesulfonamide hydrochloride

Product 1

HCID 67923715N-Methyl-4-[2-[2-(phenylthio)ethylidene]hydrazino]benzenemethanesulphonamideYield 78.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of (phenylthio)acetaldehyde (6.05 g) in absolute ethanol (180 ml) was added over 10 min to a solution of 4-hydrazino-N-methylbenzenemethanesulphonamide hydrochloride (10 g) in water (180 ml) with cooling. After addition of the aldehyde was complete, the mixture was stirred at 5° for a period of 14 h. The precipitated solid was filtered off, washed with water (200 ml), hexane (200 ml) and dried in vacuo to give the title compound (10.95 g), m.p. 110°-112°. T.l.c. (B) Rf 0.5 (KMnO4)

Workup

  1. temperaturewith cooling
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water (200 ml), hexane (200 ml)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e14be7d50ca149a4b74fff06f34dbd4f
Source dataset
uspto-grants-1991_08
Patent number
US05037845

Reaction notes

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