Sodium Carbonate → 2,4-Bis(hydroxyethylsulfonylmethyl)aniline

HRID 1087999Notes

Reaction equation

HRID 1087999 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([CH2:7][C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH2:18][CH2:19][OH:20])(=[O:17])=[O:16])[CH:11]=[CH:10][C:9]=1[N+:21]([O-])=O)(=[O:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+]>[Fe].O>[OH:1][CH2:2][CH2:3][S:4]([CH2:7][C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH2:18][CH2:19][OH:20])(=[O:17])=[O:16])[CH:11]=[CH:10][C:9]=1[NH2:21])(=[O:6])=[O:5]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 54242694HCID 54242694, compound

Product 1

HCID 536619412,4-Bis(hydroxyethylsulfonylmethyl)aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

100 parts of 2,4-bis(hydroxyethylsulfonylmethyl)nitrobenzene are added at a constant rate over a period of 30 minutes with stirring to a mixture heated to 80° to 85° C. and consisting of 40 parts of iron powder and 200 parts of water, the reaction temperature being maintained at 80° to 85° C. during the addition. After the addition is completed, stirring is continued for 30 minutes, the pH is adjusted to 8.5 with aqueous sodium carbonate solution, and the mixture is clarified while hot by removing the precipitated iron hydroxide. The filter residue is washed twice with a small amount of hot water. The combined filtrates are subsequently concentrated in vacuo to 150 parts by volume and subsequently cooled to 0° to 5° C. with stirring. The slightly brownish precipitate is isolated on a nutsche filter, covered with a small amount of ice water and dried in vacuo at 60° C. This gives 84.7 parts of 2,4-bis(hydroxyethylsulfonylmethyl)aniline of the formula ##STR23## of melting point 183° to 185° C. and a purity (by diazotization) of 99.5%.

Workup

  1. temperatureheated to 80° to 85° C.
  2. temperaturethe reaction temperature being maintained at 80° to 85° C. during the addition
  3. additionAfter the addition
  4. stirringstirring
  5. customby removing the precipitated iron hydroxide
  6. washThe filter residue is washed twice with a small amount of hot water
  7. concentrationThe combined filtrates are subsequently concentrated in vacuo to 150 parts by volume
  8. temperaturesubsequently cooled to 0° to 5° C.
  9. stirringwith stirring
  10. customThe slightly brownish precipitate is isolated on a nutsche
  11. filtrationfilter
  12. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-ebe1682ffe5d478092ad9bb7962c8086
Source dataset
uspto-grants-1990_10
Patent number
US04960940

Reaction notes

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