Acetic Anhydride → N-acetyl-2-amino-N-methyl-alpha-(3-methyl-2-thienyl)benzeneethanamine

HRID 486670

Reaktionsgleichung

Reaktionsgleichung von HRID 486670
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[CH3:17])[NH:10][CH3:11].C(O[C:22](=[O:24])[CH3:23])(=O)C>N1C=CC=CC=1>[C:22]([N:10]([CH3:11])[CH:9]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[CH3:17])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1])(=[O:24])[CH3:23]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 130176Compound 7189

Produkt 1

HCID 22414447N-acetyl-2-amino-N-methyl-alpha-(3-methyl-2-thienyl)benzeneethanamineAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A stirred, ice water chilled solution of 5.07 g of 2-amino-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine in 40 ml of pyridine was treated dropwise with 2.25 g of acetic anhydride. The solution was stirred with cooling for 15 minutes and then at room temperature for 3 hours. After standing overnight, the reaction mixture was decanted into water (200 ml), treated with dichloromethane (100 ml) and basified with 10% sodium hydroxide solution. The aqueous phase was extacted with dichloromethane (150 ml), and the combined organic phase was filtered and concentrated. The resulting solid was stirred with toluene and evaporated to dryness. Recrystallization from propionitrile (14 ml) afforded 3.0 g of N-acetyl-2-amino-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine, mp 176°-181.5° C.

Aufarbeitung

  1. temperaturewith cooling for 15 minutes
  2. waitAfter standing overnight
  3. customthe reaction mixture was decanted into water (200 ml)
  4. additiontreated with dichloromethane (100 ml)
  5. filtrationthe combined organic phase was filtered
  6. concentrationconcentrated
  7. stirringThe resulting solid was stirred with toluene
  8. customevaporated to dryness
  9. customRecrystallization from propionitrile (14 ml)

Quellen und Nachweise

ORD-Eintrag
ord-6904f10396fd43aba71c444b02a81509
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292760

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