Hydrochloric Acid → HCID 178516885, compound

HRID 1704747Notes

Reaction equation

HRID 1704747 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH:4]=[C:3]1[O:12][CH2:13][C:14]#[N:15].[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O>[NH:16]1[C:14]([CH2:13][O:12][C:3]2[C:2](=[O:1])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[O:5][CH:4]=2)=[N:15][N:18]=[N:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22758704HCID 22758704, compound

Product 1

HCID 178516885HCID 178516885, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of [(4-oxo-4H-1-benzopyran-3-yl)oxy]acetonitrile (2.0 g, 0.01 mole), sodium azide (0.715 g, 0.011 mole) and ammonium chloride (0.56 g, 0.012 mole) in DMF (10 ml) is heated at 125° C. for 7 hrs. under nitrogen. The reaction is cooled overnight and then poured into excess cold water. The aqueous is acidified with 5N hydrochloric acid and the insoluble product is filtered, washed with fresh water and sucked dry. Recrystallization from absolute ethanol gives beige colored crystals (1.45 g, 60%), mp 194°-196° C.

Workup

  1. temperatureThe reaction is cooled overnight
  2. filtrationthe insoluble product is filtered
  3. washwashed with fresh water
  4. customsucked dry
  5. customRecrystallization from absolute ethanol

Sources & evidence

ORD record
ord-75ec6efd058a426cadf5e032e2c887db
Source dataset
uspto-grants-1978_11
Patent number
US04127669

Reaction notes

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