Hydrochloric Acid → HCID 178509358, compound

HRID 2050901Notes

Reaction equation

HRID 2050901 reaction equation
[C:1]([C:3]1([C:8]#[N:9])[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C>[C:1]([C:3]1([C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 151720351,1-Dicyanocyclopentane

Product 1

HCID 178509358HCID 178509358, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1,1-biscyanocyclopentane (58 g), sodium azide (29.9 g, 460 mmoles) and ammonium chloride (28.5 g, 531 mmoles) in DMF (500 mL) was stirred and heated at 130° C. for 90 minutes. The cooled mixture was poured into 0.5 M HCl (1 liter) and extracted with ether (2×500 mL). The combined ether extracts were washed with water (2×200 mL), brine (100 mL), and dried (MgSO4). Filtration and concentration provided a solid which was recrystallized from isopropylether-hexane (16.8 g). Melting point 92°-94° C.

Workup

  1. extractionextracted with ether (2×500 mL)
  2. washThe combined ether extracts were washed with water (2×200 mL), brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and concentration
  5. customprovided a solid which
  6. customwas recrystallized from isopropylether-hexane (16.8 g)

Sources & evidence

ORD record
ord-672303a1abf24981aca4936319f3a318
Source dataset
uspto-grants-1991_05
Patent number
US05015644

Reaction notes

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