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

HRID 486670

반응식

HRID 486670 반응식
[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]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 130176Compound 7189

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6904f10396fd43aba71c444b02a81509
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292760

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