Diazomethane → HCID 12068821, compound

HRID 1823802Notes

Reaction equation

HRID 1823802 reaction equation
[OH-].[K+].[CH3:3]N(N=O)C(N)=O.[N+:10](=[CH2:12])=[N-].[C@@:13]12([OH:22])N(C)[C@@H:17]([CH2:18][CH2:19]1)[CH2:16][CH:15]=[CH:14]2>C(OCC)C.CO.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[CH3:3][N:10]1[CH:12]2[CH2:19][CH:13]([OH:22])[CH2:14][CH:15]1[CH:16]1[CH:17]2[CH2:18]1

Participants

8

Reactant 4

HCID 9550Diazomethane3×HCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 53629842Tropenol

Product 1

HCID 12068821HCID 12068821, compound

Reagents, catalysts & solvents 3

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

35 mL (0.349 mol) of 40% aqueous KOH was covered with 100 mL diethyl ether and cooled in the ice bath, and 23.64 g (0.101 mol) of N-methyl-N-nitrosourea was added batchwise, then the mixture was stirred for 10 minutes. Then the ether phase was decanted off, again combined with diethyl ether, swirled around, and decanted off. The combined organic phases were dried over solid KOH while cooling with an ice bath and the solution obtained was further used. 25 mL of the diazomethane solution prepared above and then 53.4 mg (0.000139 mol) of bis(benzonitrile)dichloropalladium(II) was added to a solution of 4.01 g (0.028 mol) of tropenol in 25 mL diethyl ether and 5 mL of methanol while cooling with an ice bath. A further 8 mL of the diazomethane solution was added, then two lots of 10 mL of diazomethane solution, each after 30 minutes, and the mixture was then stirred for another 30 minutes. The solvent was concentrated by evaporation, extracted with hot hexane, filtered hot, evaporated to dryness. Yield: 4.25 g of slightly yellowish crystals (96% of theory).

Workup

  1. additionwas added batchwise
  2. customThen the ether phase was decanted off
  3. customdecanted off
  4. dry with materialThe combined organic phases were dried over solid KOH
  5. temperaturewhile cooling with an ice bath
  6. customthe solution obtained
  7. temperaturewhile cooling with an ice bath
  8. stirringthe mixture was then stirred for another 30 minutes
  9. concentrationThe solvent was concentrated by evaporation
  10. extractionextracted with hot hexane
  11. filtrationfiltered hot
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-ab0afd90bffb422082b6b8e63c40e138
Source dataset
uspto-grants-2006_05
Patent number
US07041674B2

Reaction notes

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