Acetic Acid → HCID 21285789, compound

HRID 2231767Notes

Reaction equation

HRID 2231767 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([C:15]3[CH:20]=[CH:19][C:18]([N+]([O-])=O)=[CH:17]C=3)=[N:9][C:8]=2[N:7]([CH2:24][CH2:25][CH3:26])[C:5]1=[O:6])[CH2:2][CH3:3].C(N1C(N)=C(N)C(=O)N(CCC)C1=O)CC.[N+:43](C1C=CC(C=O)=CC=1)([O-:45])=[O:44].C(O)(=O)C>C(O)C>[CH2:24]([N:7]1[C:8](=[N:9][C:10]2[CH:15]=[CH:20][C:19]([N+:43]([O-:45])=[O:44])=[CH:18][CH:17]=2)[CH:12]([NH2:11])[C:13](=[O:14])[N:4]([CH2:1][CH2:2][CH3:3])[C:5]1=[O:6])[CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 142578718-(4-Nitrophenyl)-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 21285789HCID 21285789, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,3-Dipropyl-8-(4-nitrophenyl)xanthine, was prepared by treatment of 1,3-dipropyl-5,6-diaminouracil (1.01 g, 4.5 mmol) with 4-nitrobenzaldehyde (0.85 g, 5.6 mmol) in absolute ethanol (50 ml) in the presence of acetic acid (0.6 ml) and heated at reflux for 1 hour to yield 1,3-dipropyl-5-amino-6-(4-nitrophenyl)iminouracil. Treatment of 1,3-dipropyl-5-amino-6-(4-nitrophenyl)iminouracil (1.2 g, 3.3 mmol) with diethyl azodicarboxylate (7 ml) at 90° C. in toluene (40 ml) gave after dilution with ethanol a precipitate. This precipitate was recrystallized from ethanol yielding 0.95 g of pure product (81%). IR (KBr) 3180 (N--H), 1710(C=O), 1650(C=O), 1520(C=C) cm-1 ; Anal. Calcd. for C17H19N5O4 : MW 357.38: C, 57.14; H, 5.36; N, 19.60. Found: C, 57.22; H, 5.42; N, 19.50.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour

Sources & evidence

ORD record
ord-7a56a2a213d24ae1b5fa0330b8cedd67
Source dataset
uspto-grants-1988_11
Patent number
US04783530

Reaction notes

Loading…