Diketene → N-Methyl-N-[3-(3-methyl-1,2,4-triazolo-[4,3-b]-pyridazin-6-yl)phenyl]-3-oxo-butanamide

HRID 35640

反応式

HRID 35640 の反応式
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH3:18])=[N:16][N:17]=3)[N:14]=2)[CH:4]=1.[CH2:19]=[C:20]1[O:24][C:22](=[O:23])[CH2:21]1>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH3:18])=[N:16][N:17]=3)[N:14]=2)[CH:4]=1)[C:22](=[O:23])[CH2:21][C:20](=[O:24])[CH3:19]

参加物

4

反応物 2

HCID 12661DiketeneHCID 2779723N-Methyl-3-(3-Methyl[1,2,4]Triazolo[4,3-B]Pyridazin-6-Yl)Aniline

生成物 1

HCID 15595682N-Methyl-N-[3-(3-methyl-1,2,4-triazolo-[4,3-b]-pyridazin-6-yl)phenyl]-3-oxo-butanamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 2.0 g of N-methyl-3-(3-methyl-1,2,4-triazolo-[4,3-b]pyridazin-6-yl)benzenamine and 2.14 ml of diketene in 250 ml of dry toluene was heated to reflux for 2 days. The solution was concentrated in vacuo and the residue partitioned between 300 ml dichloromethane and 200 ml of water. The aqueous layer was extracted with 150 ml portions of dichloromethane. The organic layer and extracts were combined, dried and concentrated in vacuo. The residue was chromatographed on 300 g of silica gel with dichloromethane-methanol (97:3). The fractions containing product were combined, evaporated in vacuo and the solid recrystalized from dichloromethane-hexane to give 1.15 g of tan crystals, mp 138°-141° C.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue partitioned between 300 ml dichloromethane and 200 ml of water
  5. extractionThe aqueous layer was extracted with 150 ml portions of dichloromethane
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on 300 g of silica gel with dichloromethane-methanol (97:3)
  9. additionThe fractions containing product
  10. customevaporated in vacuo
  11. customthe solid recrystalized from dichloromethane-hexane

出典と根拠

ORDレコード
ord-d6294640900645d18814bf4b5cb8d64f
出典データセット
uspto-grants-1988_08
特許番号
US04767765

関連ノート

読み込み中…