Barbituric Acid → HCID 45102609, compound

HRID 1873643Notes

Reaction equation

HRID 1873643 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([CH2:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[CH:13]=1)=O>CO>[O:3]=[C:2]1[NH:4][C:5](=[O:6])[C:7](=[CH:10][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=3)[CH:13]=2)[C:8](=[O:9])[NH:1]1

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 8808684-[(3-formylindol-1-yl)methyl]benzonitrile

Product 1

HCID 45102609HCID 45102609, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of barbituric acid (1.28 g; 0.01 mol) and 4-((3-formyl-1H-indol-1-yl)methyl)benzonitrile (2.60 g; 0.01 mol) in methanol (50 ml) were stirred at room temperature. After 10 min the reaction mixture became a solid suspension and the color of reaction mixture changed to yellow color solid suspension. The suspension continued to stir at room temperature for 5 hrs. Solid product was separated by filtration and washed several times with cold methanol (3×5 ml). The isolated yellow solid recrystallized from methanol gave (1) as a yellow crystalline product; m.p. >300° C.; 1H NMR (DMSO-d6): δ 5.81 (s, 2H), 7.33-7.36 (m, 2H), 7.43-7.45 (d, 2H), 7.61-7.64 (m, 1H), 7.82-7.84 (d, 2H), 7.90-7.93 (m, 1H), 8.68 (s, 1H), 9.63 (s, 1H), 11.07 (bs, 1H), 11.15 (bs, 1H); 13C NMR (DMSO-d6): δ 49.7, 109.4, 110.5, 110.8, 111.8, 117.9, 118.4, 123.0, 123.8, 128.0, 129.6, 132.6, 136.1, 141.7, 141.8, 142.6, 159.2, 162.9, 164.1.

Workup

  1. customa solid suspension and the color of reaction mixture
  2. stirringto stir at room temperature for 5 hrs
  3. customSolid product was separated by filtration
  4. washwashed several times with cold methanol (3×5 ml)
  5. customThe isolated yellow solid recrystallized from methanol

Sources & evidence

ORD record
ord-d83b3fe81bb448e585c74708280c3e2c
Source dataset
uspto-grants-2012_11
Patent number
US08304421B2

Reaction notes

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