Thionyl Chloride → 3,5-Diamino-2-methylbenzoic acid

HRID 19970

Reaktionsgleichung

Reaktionsgleichung von HRID 19970
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[NH2:15])[C:9]([OH:11])=[O:10].[C:16](=O)(O)[O-].[Na+]>CO>[CH3:16][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([NH2:15])=[C:6]([NH2:5])[CH:7]=1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 692633,4-Diaminobenzoic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 1355243,5-Diamino-2-methylbenzoic acidAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To dry methanol (20 ml) was carefully added thionyl chloride (1 ml) dropwise with stirring. The 3,4-diaminobenzoic acid (1 g) was added in portions at R.T. with stirring then the mixture heated at reflux for 3 h. Saturated sodium bicarbonate was added until the mixture was basic, then the mixture extracted into chloroform containing 25% methanol. The extract was dried and evaporated in vacuo to give the product (0.88 g, 81%) as a brown crystalline solid.

Aufarbeitung

  1. stirringwith stirring
  2. temperaturethe mixture heated
  3. temperatureat reflux for 3 h
  4. extractionthe mixture extracted into chloroform containing 25% methanol
  5. customThe extract was dried
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-79f45971a6444b508008851ae0cf9325
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745490B2

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