3-Nitrobenzenesulfonyl chloride → HCID 54066048, compound

HRID 1389962Notes

Reaction equation

HRID 1389962 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:14][CH2:15][CH2:16][O:17][S:18](=[O:21])(=[O:20])[OH:19].[OH-].[Na+]>O>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:14][CH2:15][CH2:16][O:17][S:18](=[O:20])(=[O:19])[OH:21])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 70223Aminoethyl sulfate

Product 1

HCID 54066048HCID 54066048, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

221.5 g of 3-nitro-benzenesulphonyl chloride are introduced in portions into a solution of 150 g of sulphuric acid mono-2-amino-ethyl ester and 0.6 liter of water at 60°-70° C. During this procedure, the pH value is continuously kept between 9.0 and 10.0 by adding 45% strength sodium hydroxide solution dropwise. The mixture is subsequently stirred at 60°-70° C. and pH 9.0 to 10.0 for 1 hour and then allowed to cool and the resulting precipitate is filtered off. The precipitate is washed with water and dried at 80° C. 305 g of sulphuric acid mono-N-(3-nitro-benzenesulphonyl)-2-amino-ethyl ester are obtained. This ester is dissolved in 1.5 liters of dimethylformamide and hydrogenated over Raney nickel. After subsequently filtering off the catalyst and distilling off the solvent in vacuo, about 220 g of sulphuric acid mono-N-(3-aminophenylsulphonyl)-2-aminoethyl ester are obtained. ##STR16##

Workup

  1. temperatureto cool
  2. filtrationthe resulting precipitate is filtered off
  3. washThe precipitate is washed with water
  4. customdried at 80° C

Sources & evidence

ORD record
ord-2b2f9b0c29da462daba6f60661d97338
Source dataset
uspto-grants-1981_01
Patent number
US04247460

Reaction notes

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