Adiponitrile → HCID 178510971, compound

HRID 503020Notes

Reaction equation

HRID 503020 reaction equation
[C:1](#[N:8])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].[N-:9]=[N+:10]=[N-:11].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH:7]1[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][C:1]#[N:8])=[N:11][N:10]=[N:9]1

Participants

5

Reactant 3

HCID 8128AdiponitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 178510971HCID 178510971, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of adiponitrile (249 g, 2.3 mol) in DMF (400 mL) was stirred as sodium azide (30 g, 460 mmol) and ammonium chloride (24.7 g, 461 mmol) were added. The reaction was heated at 120° C. for 48 h. The reaction was allowed to cool and concentrated. The residue was dissolved in aqueous ether. The aqueous layer was washed with ether (2×). The combined ether layers were concentrated to afford 1H-tetrazole-5-pentanenitrile as a white solid.

Workup

  1. additionwere added
  2. temperatureto cool
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in aqueous ether
  5. washThe aqueous layer was washed with ether (2×)
  6. concentrationThe combined ether layers were concentrated

Sources & evidence

ORD record
ord-b0d47724fdc64779acad04b0ff30134c
Source dataset
uspto-grants-2010_08
Patent number
US07776896B2

Reaction notes

Loading…