Hydrochloric Acid → HCID 178466632, compound

HRID 1609264Notes

Reaction equation

HRID 1609264 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[O:10][CH:11]([CH3:14])[C:12]#[N:13])([O-:3])=[O:2].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[O:10][CH:11]([C:12]1[NH:24][N:23]=[N:22][N:13]=1)[CH3:14])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 200844962-[3-(2-Nitrophenoxy)phenoxy]propionitrile

Product 1

HCID 178466632HCID 178466632, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

In 25 ml of N,N-dimethylformamide was dissolved 2.0 g of the 2-[3-(2-nitrophenoxy)phenoxy]propionitrile followed by addition of 0.92 g of sodium azide and 0.76 g of ammonium chloride, and the mixture was stirred at 115° C. for 80 minutes. The reaction mixture was then poured into ice-water containing 3 ml of concentrated hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried and concentrated to give 2.4 g of the title compound as a light brown oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d7bc2f31a45b48e8b9fc6da216193659
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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