Sulfuric Acid → N-(3-Hydroxy-2,6-dimethylphenyl)acetamide

HRID 579971

Reaktionsgleichung

Reaktionsgleichung von HRID 579971
[C:1]([NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7](N)[C:6]=1[CH3:13])(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:15].N([O-])=O.[Na+].NC(N)=O.[Cl-].[Na+]>O>[C:1]([NH:4][C:5]1[C:6]([CH3:13])=[C:7]([OH:15])[CH:8]=[CH:9][C:10]=1[CH3:11])(=[O:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 1118Sulfuric AcidHCID 1176UreaHCID 5234Sodium ChlorideHCID 847848N-(3-amino-2,6-dimethylphenyl)acetamideHCID 23668193Sodium Nitrite

Produkt 1

HCID 10419764N-(3-Hydroxy-2,6-dimethylphenyl)acetamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Versuchsvorschrift

1-Acetamido-3-amino-2,6-dimethylbenzene (4.77 g; 26.8 mmol) was dissolved in a diluted acid prepared from concentrated sulfuric acid (3 ml) and water (30 ml). To the resulting solution was added dropwise a solution of sodium nitrite (2.40 g; 34.8 mmol) in water (5 ml) in a manner such that the temperature of the reaction mixture did not exceed 10° C. Then, the mixture was stirred under ice-cooling for 15 minutes. After addition of 1.00 g of urea (16.6 mmol), the mixture was dropwise added gradually into 75 ml of boiling water and the whole mixture was refluxed for 30 minutes. After cooling, sodium chloride was added, followed by extraction with ether and chloroform. The organic layer was washed with water and dried over magnesium sulfate (dehydration), and the solvent was distilled off to give 3.2 g (67%) of the title compound as colorless needles, m.p. 190°-195° C.

Aufarbeitung

  1. customdid not exceed 10° C
  2. temperaturecooling for 15 minutes
  3. temperaturethe whole mixture was refluxed for 30 minutes
  4. temperatureAfter cooling
  5. extractionfollowed by extraction with ether and chloroform
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate (dehydration)
  8. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-678fdb5ec758429d970ca78ab89e6193
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04751232

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