Hydrochloric Acid → HCID 67797545, compound

HRID 569920Notes

Reaction equation

HRID 569920 reaction equation
[CH3:1][C:2]1[C:3]2[CH2:14][CH2:13][C:8]3[N:9]([CH3:12])[N:10]=[CH:11][C:7]=3[C:4]=2[NH:5][N:6]=1.[H-].[Na+].I[CH3:18].[ClH:19]>CN(C)C=O.C(OCC)C>[ClH:19].[CH3:18][N:5]1[C:4]2[C:7]3[CH:11]=[N:10][N:9]([CH3:12])[C:8]=3[CH2:13][CH2:14][C:3]=2[C:2]([CH3:1])=[N:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178434170HCID 178434170, compound

Product 1

HCID 67797545HCID 67797545, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 14.5 g of 1,4,5,6-tetrahydro-3,6-dimethylbenzo[1,2-c:3,4-c']dipyrazole in 50 ml of dimethylformamide was added to an ice-cold stirred suspension of 2.4 g of sodium hydride in 50 ml of dimethylformamide. The reaction was stirred at 0° C. for 20 minutes and then a solution of 6.3 ml of iodomethane in 15 ml of dimethylformamide was added dropwise. The mixture was allowed to come to room temperature and stirred for 2 hours. The solvent was evaporated under reduced pressure and the residue partitioned between dichloromethane and water. The aqueous layer was extracted exhaustively with dichloromethane and the combined dichloromethane extracts were dried over magnesium sulfate and concentrated under reduced pressure. The residue was flash chromatographed (7.5% 2-propanol in dichloromethane) to give crude product. This crude mixture was dissolved in ethyl ether and acidified with ethereal hydrogen chloride. The cream color precipitate which formed was recrystallized from 2-butanol to give 1,4,5,6- tetrahydro-1,3,6-trimethylbenzo[1,2-c:3,4-c']dipyrazole monohydrochloride as light-yellow granules (20% yield) melting at about 252°-254° C.

Workup

  1. stirringThe reaction was stirred at 0° C. for 20 minutes
  2. customto come to room temperature
  3. stirringstirred for 2 hours
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue partitioned between dichloromethane and water
  6. extractionThe aqueous layer was extracted exhaustively with dichloromethane
  7. dry with materialthe combined dichloromethane extracts were dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customchromatographed (7.5% 2-propanol in dichloromethane)
  10. customto give crude product
  11. customThe cream color precipitate which formed
  12. customwas recrystallized from 2-butanol

Sources & evidence

ORD record
ord-c05df8d52b08438b8c4f5e287ac68e27
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Reaction notes

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