Hydrochloric Acid → HCID 178515803, compound

HRID 1603883Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8-nitro-4-oxo-4H-1-benzopyran-2-carbonitrile (1.094 g, 5.06 mmol), sodium azide (1.638 g, 25.3 mmol), ammonium chloride (1.349 g, 25.3 mmol) and dry N,N-dimethylformamide (50 ml) was left under stirring at 100° C. for 1.25 h. After that the mixture was cooled at room temperature and poured onto a 1M hydrochloric acid solution (50 ml) recovering the formed precipitate by filtration. The resulting solid was suspended in concentrated hydrochloric acid (12 ml) stirring at room temperature for 2.5 h. After this time the acid mixture was diluted with water (50 ml) and extracted with ethyl acetate (4×30 ml). The organic phase was dried and the solvent was evaporated off under reduced pressure, thereby obtaining 0.896 g of the title product (69% yield).

Workup

waitwas left
temperatureAfter that the mixture was cooled at room temperature
customrecovering the formed precipitate
filtrationby filtration
stirringstirring at room temperature for 2.5 h
additionAfter this time the acid mixture was diluted with water (50 ml)
extractionextracted with ethyl acetate (4×30 ml)
customThe organic phase was dried
customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record: ord-2cd0be31ca8c496bba8c942cdb0d1e09
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990142

Reaction notes

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