Methyl iodide → HCID 14128511, compound

HRID 569898Notes

Reaction equation

HRID 569898 reaction equation
[CH3:1][N:2]1[C:6]2[CH2:7][CH2:8][CH2:9][C:10]3[NH:11][N:12]=[CH:13][C:14]=3[C:5]=2[CH:4]=[N:3]1.[H-].[Na+].[CH3:17]I>CN(C)C=O>[CH3:1][N:2]1[C:6]2[CH2:7][CH2:8][CH2:9][C:10]3[N:11]([CH3:17])[N:12]=[CH:13][C:14]=3[C:5]=2[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14128510HCID 14128510, compound

Product 1

HCID 14128511HCID 14128511, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A mixture of 19.4 g of 4,5,6,7-tetrahydro-3-methyl-3H-cyclohepta[1,2-c:4,3-c']dipyrazole in 70 ml of N,N-dimethylformamide was added, dropwise, to a suspension of 2.64 g of sodium hydride in 200 ml of N,N-dimethylformamide and the resulting mixture was stirred at room temperature for 15 minutes. A solution of 12.5 ml of methyl iodide in 20 ml of N,N-dimethylformamide was added dropwise and the reaction mixture was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane and water. The aqueous layer was extracted several times with dichloromethane and the combined dichloromethane layers were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a tan powder which was shown to be a 50:50 mixture of the 2,7-dimethyl and 3,7-dimethyl products as shown by 1H NMR. The tan powder was recrystallized from toluene to give a tan solid which was again recrystallized from toluene to give 4,5,6, 7-tetrahydro-3,7-dimethyl-3H-cyclohepta[1,2-c:4,3-c']dipyrazole as tan needles melting at about 191°-195° C.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between dichloromethane and water
  5. extractionThe aqueous layer was extracted several times with dichloromethane
  6. washthe combined dichloromethane layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a tan powder which
  10. customThe tan powder was recrystallized from toluene
  11. customto give a tan solid which
  12. customwas again recrystallized from toluene

Sources & evidence

ORD record
ord-c6f300b1e07649a6a010d07c1571ea67
Source dataset
uspto-grants-1988_03
Patent number
US04734429

Reaction notes

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