Hydrazine hydrate (1:1) → 4-ethoxy-N-(2-hydrazino-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamide

HRID 971310Notes

Reaction equation

HRID 971310 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.O.[NH2:27][NH2:28]>CO>[CH2:23]([O:22][C:19]1[CH:20]=[CH:21][C:16]([S:13]([N:5]([CH2:4][C:3]([NH:27][NH2:28])=[O:2])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)(=[O:15])=[O:14])=[CH:17][CH:18]=1)[CH3:24]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1108126Methyl{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}acetate

Product 1

HCID 102700744-ethoxy-N-(2-hydrazino-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude carboxylic acid methyl ester, e.g. methyl{[(4-ethoxyphenyl)sulfonyl]-4-methylanilino}acetate (3.816 g, 10.5 mmol), was dissolved in MeOH (30 mL). Hydrazine hydrate was added (3.3 mL). The reaction mixture was stirred overnight at room temperature. A white precipitate was formed. It was isolated by filtration and rinsed with cold MeOH. From mother liquors some more compound could be recovered, affording the desired product, e.g. 4-ethoxy-N-(2-hydrazino-2-oxoethyl)-N-(4-methylphenyl)benzenesulfonamide (2.745 g, 72%) as a colorless solid in 99.8% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customA white precipitate was formed
  2. customIt was isolated by filtration
  3. washrinsed with cold MeOH
  4. customFrom mother liquors some more compound could be recovered

Sources & evidence

ORD record
ord-d94437a0a07249d8b7b56d3c40a37088
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

Loading…