Methyl iodide → HCID 70873098, compound

HRID 1526125Notes

Reaction equation

HRID 1526125 reaction equation
[Na].[C:2]([C:4]1[C:9](=[S:10])[NH:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:30]([O-:32])=[O:31])#[N:3].[CH3:33]I>CO>[C:2]([C:4]1[C:9]([S:10][CH3:33])=[N:8][C:7]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[C:6]([C:5]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:30]([O-:32])=[O:31])[C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5360545Sodium2×HCID 70874350HCID 70874350, compound

Product 1

HCID 70873098HCID 70873098, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

69 mg (3 mmol) of sodium is added at room temperature in small portions to 0.4 ml of methanol. After the sodium disappears, 870 mg (2 mmol) of ethyl 5-cyano-2-(4-methoxyphenyl)-4-(2-nitrophenyl)-6-thioxo-1,6-dihydropyridine-3-carboxylate is added. The reaction mixture is stirred for 5 minutes, and then 0.18 ml (3 mmol) of methyl iodide is added and stirring is continued for 3 hours. The solvent is concentrated and the precipitate formed is filtered, rinsed with water and then diethyl ether and then dried under vacuum to yield 0.53 g (59%) of ethyl 5-cyano-2-(4-methoxyphenyl)-6-(methylthio)-4-(2-nitrophenyl)nicotinate in the form of a yellow powder.

Workup

  1. stirringstirring
  2. waitis continued for 3 hours
  3. concentrationThe solvent is concentrated
  4. customthe precipitate formed
  5. filtrationis filtered
  6. washrinsed with water
  7. dry with materialdiethyl ether and then dried under vacuum

Sources & evidence

ORD record
ord-a7b18f83d7db451aad1ca62bf52c7513
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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