Ammonia → HCID 14126714, compound

HRID 569919Notes

Reaction equation

HRID 569919 reaction equation
C([N:8]1[C:12]2[CH2:13][C:14]3[CH:18]=[N:17][NH:16][C:15]=3[C:11]=2[CH:10]=[N:9]1)C1C=CC=CC=1.N.[Na].[Cl-].[NH4+]>O1CCCC1>[NH:8]1[C:12]2[CH2:13][C:14]3[CH:18]=[N:17][NH:16][C:15]=3[C:11]=2[CH:10]=[N:9]1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 57099057HCID 57099057, compound

Product 1

HCID 14126714HCID 14126714, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-32 °C

Procedure

A solution was prepared from 5.8 g of 1-benzyl-4,7- dihydro-1H-cyclopenta[1,2-c:3,4-c']dipyrazole in 150 ml of tetrahydrofuran and 300 ml of liquid ammonia at -78° C. Sodium metal (2.8 g) was added in small pieces and the reaction was stirred at -32° C. for 1.5 hours. Ammonium chloride (10 g) was added and the ammonia was allowed to evaporate over a period of 20 minutes. The residual reaction mixture was filtered and the filter cake was washed with ethanol. The combined filtrates were then concentrated under reduced pressure and the residue was triturated with ethyl acetate to give 4,7-dihydro-1H-cyclopenta[1,2-c:3,4-c']dipyrazole as a tan granular solid (50% yield) melting at about 180° C. with decomposition

Workup

  1. customto evaporate over a period of 20 minutes
  2. customThe residual reaction mixture
  3. filtrationwas filtered
  4. washthe filter cake was washed with ethanol
  5. concentrationThe combined filtrates were then concentrated under reduced pressure
  6. customthe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-597c878c378d4f648ec7490badd5c999
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Reaction notes

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