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Hydrochloric Acid → 3-(N-methylamino)aniline-4-sulfonic acid

HRID 1197210
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1197210
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[C:4]([NH2:12])[CH:3]=1.[C:13](OC(=O)C)(=O)C.[OH-].[Na+].S(OC)(OC)(=O)=O.Cl.[Cl-].[Na+]>O.C(O)=O>[CH3:13][NH:12][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[S:8]([OH:11])(=[O:9])=[O:10])[NH2:1]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6497Dimethyl SulfateHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide3×HCID 666232,4-Diaminobenzenesulfonic acid

Produkt 1

HCID 10965570
3-(N-methylamino)aniline-4-sulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

94 g of 1,3-diaminobenzene-4-sulfonic acid in 430 ml of water and 70 g of formic acid were boiled for 3 hours under reflux. The mixture was cooled to 20° C., and the resulting 3-(N-formylamino)aniline-4-sulfonic acid was filtered off in vacuo and stirred in 500 g of water with the addition of caustic soda solution to give a pH of 6.5. 70 g of acetic anhydride were then added and the pH was kept between 5.0 and 6.5 by the addition of caustic soda solution. After 30 minutes, the pH was adjusted to 12.5 with caustic soda solution, and 75 g of dimethyl sulfate were added dropwise. After 30 minutes, the pH was adjusted to -0.5 with hydrochloric acid, and the mixture was boiled under reflux for 3 hours. After cooling, the mixture was adjusted to pH 1.0 with caustic soda solution and salted out with 150 g of sodium chloride. The precipitated 3-(N-methylamino)aniline- 4-sulfonic acid was isolated by filtration in vacuo.

Aufarbeitung

  1. temperatureunder reflux
  2. filtrationthe resulting 3-(N-formylamino)aniline-4-sulfonic acid was filtered off in vacuo
  3. customto give a pH of 6.5
  4. additionwere added dropwise
  5. waitAfter 30 minutes
  6. temperatureunder reflux for 3 hours
  7. temperatureAfter cooling

Quellen und Nachweise

ORD-Eintrag
ord-d46403aea0164f58b488fbb708d4e92a
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05117050

Notizen zur Reaktion

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