Ammonium Chloride → HCID 178458282, compound

HRID 1017696Notes

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 recrystallized 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 recrystallized from ethanol (with charcoal)

Sources & evidence

ORD record: ord-baf79a49aed94635a7cd7130f3e1490f
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479520B1

Reaction notes

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