Ethanol → HCID 70874350, compound

HRID 1526124Notes

Reaction equation

HRID 1526124 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.C(O)C.N1C=CC=CC=1.[C:26]([C:28](=[CH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])[C:29](=[S:31])[NH2:30])#[N:27]>C(N(CC)CC)C>[C:26]([C:28]1[C:29](=[S:31])[NH:30][C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:32]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])#[N:27]

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl esterHCID 28911832-Propenethioamide, 2-cyano-3-(2-nitrophenyl)-

Product 1

HCID 70874350HCID 70874350, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.22 g (10 mmol) of ethyl 3-(4-methoxyphenyl)-3-oxopropanoate, 50 ml of ethanol, 5 ml of pyridine and 0.5 ml of triethylamine are added respectively to 2.33 g (10 mmol) of 2-cyano-3-(2-nitrophenyl)prop-2-enethioamide. The reaction mixture is stirred at reflux for 5 hours. After returning to room temperature, the solvent is evaporated and the reaction mixture is poured over crushed ice. Acetic acid is added until an acidic pH (2 to 3) is obtained. The precipitate formed is filtered, rinsed with water and diethyl ether, and then dried under vacuum to yield 4.35 g (92%) of ethyl 5-cyano-2-(4-methoxyphenyl)-4-(2-nitrophenyl)-6-thioxo-1,6-dihydropyridine-3-carboxylate in the form of a yellow powder.

Workup

  1. temperatureat reflux for 5 hours
  2. customAfter returning to room temperature
  3. customthe solvent is evaporated
  4. additionthe reaction mixture is poured
  5. customover crushed ice
  6. additionAcetic acid is added until an acidic pH (2 to 3)
  7. customis obtained
  8. customThe precipitate formed
  9. filtrationis filtered
  10. washrinsed with water and diethyl ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-0254ffdc0c21408d97feb98cf167ac4f
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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