Ethyl cyanoacetate → HCID 9884770, compound

HRID 1370275Notes

Reaction equation

HRID 1370275 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH2:20])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[O-]CC.[Na+].[C:25]([CH2:27][C:28](OCC)=[O:29])#[N:26]>C(O)C>[NH2:26][C:25]1[N:10]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[S:12][C:11]2=[N:20][C:28](=[O:29])[CH:27]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 30248982-Thiazolamine, 4-(4-methoxyphenyl)-5-(4-pyridinyl)-

Product 1

HCID 9884770HCID 9884770, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of [4-(4-methoxyphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl]amine (1.0 g) in ethanol were added in turn a 20% solution of sodium ethoxide in ethanol (1.4 mL) and ethyl cyanoacetate (0.40 g). The resultant mixture was heated under reflux for 8 hours. After distilling off the solvent, water was added to the residue, the mixture was neutralized with acetic acid and the precipitate formed was filtered off. The remaining crude crystals were recrystallized from ethanol to obtain the title compound (0.52 g, yield 42%).

Workup

  1. temperatureunder reflux for 8 hours
  2. distillationAfter distilling off the solvent, water
  3. additionwas added to the residue
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. customThe remaining crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-239dcf05877540fe80e2668b9938892d
Source dataset
uspto-grants-2003_06
Patent number
US06583146B1

Reaction notes

Loading…