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

HRID 1906812Notes

Reaction equation

HRID 1906812 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ff64e31217bd4592ac66a2db5ef61883
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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