2-Propenoic acid, 3-(4-formylphenyl)- → HCID 178481362, compound

HRID 1638327Notes

Reaction equation

HRID 1638327 reaction equation
O.[NH2:2][C:3]1[C:4](=[O:13])[N:5]([CH3:12])[C:6](=[O:11])[N:7]([CH3:10])[C:8]=1[NH2:9].[CH:14]([C:16]1[CH:26]=[CH:25][C:19]([CH:20]=[CH:21][C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1)=O>[N+](C1C=CC=CC=1)([O-])=O>[CH3:12][N:5]1[C:4](=[O:13])[C:3]2[N:2]=[C:14]([C:16]3[CH:26]=[CH:25][C:19](/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])=[CH:18][CH:17]=3)[NH:9][C:8]=2[N:7]([CH3:10])[C:6]1=[O:11]

Participants

4

Reactant 2

HCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 122574835,6-diamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione hydrate

Product 1

HCID 178481362HCID 178481362, compound

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent3×

Procedure

5,6-Diamino-1,3-dimethyluracil hydrate (5.11 g, 30.0 mmol) and 4-formylcinnamic acid (5.29 g, 30.0 mmol) were refluxed in nitrobenzene (500 mL). The nitrobenzene was allowed to distill slowly with water formed. Fresh nitrobenzene was added to keep the volume constant. After 5 hours of reflux, the mixture was cooled and the precipitate collected (8.07 g). Recrystallization from N,N-dimethylformamide-water gave the monohydrate of the title compound as a pale yellow powder, identical with that of Example 1 by 1H-NMR and elemental analysis.

Workup

  1. distillationto distill slowly with water
  2. customformed
  3. temperatureAfter 5 hours of reflux
  4. temperaturethe mixture was cooled
  5. customthe precipitate collected (8.07 g)
  6. customRecrystallization from N,N-dimethylformamide-water

Sources & evidence

ORD record
ord-adb3fe17e1fb45db8ed9a4d41a6f8ae8
Source dataset
uspto-grants-1989_11
Patent number
US04879296

Reaction notes

Loading…