Malononitrile → HCID 15027644, compound

HRID 1090646Notes

Reaction equation

HRID 1090646 reaction equation
[CH:1]([C:3]1[C:8](=[O:9])[N:7]([CH2:10][CH2:11][CH3:12])[C:6](=[O:13])[N:5]2[CH2:14][CH2:15][S:16][C:4]=12)=O.[C:17](#[N:21])[CH2:18][C:19]#[N:20].[OH-].[K+]>C(O)C>[C:19]([C:18](=[CH:1][C:3]1[C:8](=[O:9])[N:7]([CH2:10][CH2:11][CH3:12])[C:6](=[O:13])[N:5]2[CH2:14][CH2:15][S:16][C:4]=12)[C:17]#[N:21])#[N:20]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 14797Potassium HydroxideHCID 15027643HCID 15027643, compound

Product 1

HCID 15027644HCID 15027644, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 8-formyl-6-propyl-2,3-dihydro-5H-thiazolo[3,2-c]pyrimidine-5,7(6H)-dione(1 g), malononitrile (0.31 g) and ethanol (20 ml) containing 10% aqueous solution of potassium hydroxide (0.1 ml), were stirred at 60° C. for 7 hours. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in chloroform. After washing with water and drying, the organic solution was concentrated to dryness. The resulting residue was purified by column chromatography on silica gel. The resulting crude crystals were recrystallized from ethyl acetate-isopropyl ether to give pale yellow-red needles (0.23 g, 19%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. washAfter washing with water
  4. customdrying
  5. concentrationthe organic solution was concentrated to dryness
  6. customThe resulting residue was purified by column chromatography on silica gel
  7. customThe resulting crude crystals were recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-83730fda0d334200818673f7fd9c19a5
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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