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

HRID 486670

Reaction equation

HRID 486670 reaction equation
[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]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 130176Compound 7189

Product 1

HCID 22414447N-acetyl-2-amino-N-methyl-alpha-(3-methyl-2-thienyl)benzeneethanamineYield 50.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-6904f10396fd43aba71c444b02a81509
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Linked notes

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