Hydrochloric Acid → HCID 178526592, compound

HRID 1609267Notes

Reaction equation

HRID 1609267 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])([O-:3])=[O:2].[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([C:10]2[NH:21][N:20]=[N:19][N:11]=2)[CH:12]=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 91948883-(2-Nitrophenoxy)benzonitrile

Product 1

HCID 178526592HCID 178526592, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

In 40 ml of N,N-dimethylformamide was dissolved 4.0 g of 3-(2-nitrophenoxy)benzonitrile followed by addition of 2.28 g of sodium azide and 1.88 g of ammonium chloride, and the mixture was stirred at 110° C. for 4 hours. After cooling, the reaction mixture was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water twice, dried and concentrated. The residue was crystallized from ethyl acetate-benzene to give 3.6 g of the title compound as light brown crystals.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water twice
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was crystallized from ethyl acetate-benzene

Sources & evidence

ORD record
ord-fa2bc5443d2546c49f0fa1182e85156d
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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