Ammonium Chloride → HCID 178458282, compound

HRID 1656390Notes

Reaction equation

[C:1]([C:3]1[C:4](=[O:19])[NH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH2:16][CH2:17][CH3:18])=[CH:7][CH:8]=1)#[N:2].[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>CN(C)C=O>[CH2:16]([O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[NH:5][C:4](=[O:19])[C:3]([C:1]2[NH:22][N:21]=[N:20][N:2]=2)=[CH:8][CH:7]=1)[CH2:17][CH3:18]

Participants

Conditions

Temperature: 120 °C

Procedure

A stirred mixture of 3-cyano-6-(2-propoxyphenyl)-2-(1H)-pyridinone (1.85 g), sodium azide (0.59 g), ammonium chloride (0.49 g) and lithium chloride (0.39 g) in dry dimethylformamide (75 ml) was heated at 120° C. for 72 hours. The reaction mixture was evaporated to dryness and the resultant residue treated with water (100 ml) and acidified with glacial acetic acid to afford a precipitate which was collected and dissolved in warm dilute aqueous potassium bicarbonate. The aqueous solution was allowed to stand overnight at room temperature, was filtered and the filtrate was acidified with concentrated hydrochloric acid to afford a yellow precipitate, 1.80 g, m.p. 226°-230° C. This was recrystallised from ethanol (with charcoal) to afford the pure title compound, 1.08 g, m.p. 229°-231° C.

Workup

customThe reaction mixture was evaporated to dryness
additionthe resultant residue treated with water (100 ml)
customto afford a precipitate which
customwas collected
dissolutiondissolved
temperaturein warm dilute aqueous potassium bicarbonate
filtrationwas filtered
customto afford a yellow precipitate, 1.80 g, m.p. 226°-230° C
customThis was recrystallised from ethanol (with charcoal)

Sources & evidence

ORD record: ord-3494481e3b734200af127c3bb09a5d64
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254571

Reaction notes

Loading…