Acetic Acid → HCID 14257873, compound

HRID 2231768Notes

Reaction equation

[CH2:1]([N:4]1[C:11]([NH2:12])=[C:10]([NH2:13])[C:8](=[O:9])[N:7]([CH2:14][CH2:15][CH3:16])[C:5]1=[O:6])[CH2:2][CH3:3].[C:17]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)#[N:18].C(O)(=O)C.[K+].[Br-]>C(O)C>[CH2:14]([N:7]1[C:8](=[O:9])[C:10]2[NH:13][C:23]([C:22]3[CH:25]=[CH:26][C:19]([C:17]#[N:18])=[CH:20][CH:21]=3)=[N:12][C:11]=2[N:4]([CH2:1][CH2:2][CH3:3])[C:5]1=[O:6])[CH2:15][CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

1,3-Dipropyl-8-(4-cyanophenyl)xanthine was prepared by treatment of 1,3-dipropyl-5,6-diaminouracil (6.37 g, 28.15 mmol) with 4-cyanobenzaldehyde (3.72 g, 28.37 mmol) in absolute ethanol (175 ml) with acetic acid (5 ml) heated at reflux for 2 hours. The reaction mixture was then cooled to 0° C., and the resulting precipitate collected, and recrystallized from ethanol yielding a white solid (8.1 g, 24.0 mmol, 85%) IR (KBr) 3142 (N--H), 2965 (C--H), 2232 (C=N), 1695 (C=O), 1651 (C=O) cm-1 ; 1H NMR (DMSO d6) δ8.2 (d,J=8 Hz, 6H). Anal. Calcd. for C18H19N4O21, MW. 337.38: C, 64.08; H, 5.68; N, 20.76. Found: C, 64.15, H, 5.69; N, 20.72.

Workup

temperatureheated
temperatureat reflux for 2 hours
customthe resulting precipitate collected

Sources & evidence

ORD record: ord-38b06ae8bb15473b83d09f54870da146
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04783530

Reaction notes

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