Ammonium Chloride → HCID 86745117, compound

HRID 344768Notes

Reaction equation

HRID 344768 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[CH:7]1[O:14][CH:6]21)#[N:2].[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C@@H:7]([OH:14])[C@@H:6]2[N:15]=[N+:16]=[N-:17])#[N:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14896383HCID 14896383, compound

Product 1

HCID 86745117HCID 86745117, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-cyano-1,1-dimethyl-2,3-epoxyindane (1.34g), sodium azide (0.533g), and ammonium chloride (0.44g) in dry N,N-dimethylformamide (20 ml) was stirred and heated at 60° C., under nitrogen, for 3h. The mixture was diluted with water, and extracted with ethyl acetate. The combined organic layers were washed with water, brine, and then dried (Na2SO4). Removal of solvents in vacuo, followed by chromatography of the residue (Si gel, eluted with 30% EtOAc in pentane) gave the title compound as a gum (0.93g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customRemoval of solvents in vacuo
  5. washfollowed by chromatography of the residue (Si gel, eluted with 30% EtOAc in pentane)

Sources & evidence

ORD record
ord-dbbef10e8c84490392d808dac7c25fb4
Source dataset
uspto-grants-1991_10
Patent number
US05053427

Reaction notes

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