3-amino-N-(2-hydroxyethyl)benzenesulfonamide → 2-[(3-Aminobenzene-1-sulfonyl)amino]ethyl hydrogen sulfate

HRID 1389963Notes

Reaction equation

HRID 1389963 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH2:12][CH2:13][OH:14])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.O.[S:16](=O)(=[O:19])([OH:18])[OH:17]>>[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH2:12][CH2:13][O:14][S:16](=[O:18])(=[O:17])[OH:19])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 4587823-amino-N-(2-hydroxyethyl)benzenesulfonamideHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 536717822-[(3-Aminobenzene-1-sulfonyl)amino]ethyl hydrogen sulfate

Procedure

216 g of 3-amino-N-(2-hydroxyethyl)-benzenesulphonamide are stirred into 0.4 liter of sulphuric acid monohydrate at 0°-5° C., whilst cooling. The mixture is subsequently stirred, first at 0°-5° C. for 1 hour and then at 15°-20° C. for 3 hours. The solution is then discharged onto about 2.5 liters of ice-water, the temperature being kept below 5° C. The resulting precipitate is allowed to settle, the sulphuric acid solution is largely distilled off, the reaction product is filled up to a volume of about 1 liter with ice-water, the mixture is neutralised by adding 45.0% strength sodium hydroxide solution dropwise, whilst cooling, and the resulting precipitate is filtered off. It is washed with a little water and can be employed in the subsequent diazotisation reaction as a moist paste. If the precipitate is dried, about 200 g of sulphuric acid mono-N-(3-amino-phenylsulphonyl)-2-aminoethyl ester are obtained. ##STR17##

Workup

  1. temperaturewhilst cooling
  2. waitat 15°-20° C. for 3 hours
  3. custombeing kept below 5° C
  4. distillationthe sulphuric acid solution is largely distilled off
  5. additionthe reaction product is filled up to a volume of about 1 liter with ice-water
  6. additionby adding 45.0% strength sodium hydroxide solution dropwise
  7. temperaturewhilst cooling
  8. filtrationthe resulting precipitate is filtered off
  9. washIt is washed with a little water
  10. customcan be employed in the subsequent diazotisation reaction as a moist paste
  11. customIf the precipitate is dried

Sources & evidence

ORD record
ord-f8acb0d926c44b49a91d625be0f92c31
Source dataset
uspto-grants-1981_01
Patent number
US04247460

Reaction notes

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