Potassium tert-butoxide → HCID 69117970, compound

HRID 889828Notes

Reaction equation

HRID 889828 reaction equation
[CH3:1][N:2]([CH2:7][C:8](=[N:16][NH2:17])[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:3](OC)=[O:4].CC(C)([O-])C.[K+]>O1CCCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]2[CH2:7][N:2]([CH3:1])[C:3](=[O:4])[NH:17][N:16]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86590933HCID 86590933, compound

Product 1

HCID 69117970HCID 69117970, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

68.24 g (267 mmol) of 2-(N-methyl-N-(methoxycarbonyl)-amino)-4′-chloroacetophenone hydrazone was dissolved in 400 ml of tetrahydrofuran. To this solution was added 30 ml of 20% potassium tert-butoxide in tetrahydrofuran. The resulting reaction mixture was refluxed for two hours, concentrated in vacuo, slurried in 500 ml of 50/50 diethyl ether/hexanes and filtered. The golden solid was washed with water and dried yielding 30 g of the title compound, mp 195–197° C.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for two hours
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered
  5. washThe golden solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-a706a18c4b4f434ea09a0a38faca530f
Source dataset
uspto-grants-2006_02
Patent number
US06995157B2

Reaction notes

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