Isonicotinic acid, 2-chloro-3-cyano-6-methyl-, ethyl ester → HCID 178469058, compound

HRID 488916Notes

Reaction equation

HRID 488916 reaction equation
[NH2:1][C:2](N)=[S:3].[CH2:5]([O:7][C:8](=[O:19])[C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11](Cl)[C:10]=1C#N)[CH3:6]>CCO>[CH2:5]([O:7][C:8](=[O:19])[C:9]1[CH:14]=[C:13]([CH3:15])[N:1]=[C:2]([SH:3])[C:10]=1[C:11]#[N:12])[CH3:6]

Participants

4

Reactant 2

HCID 142408Isonicotinic acid, 2-chloro-3-cyano-6-methyl-, ethyl esterHCID 2723790Thiourea

Product 1

HCID 178469058HCID 178469058, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (339 mg, 4.46 mmol) was added to a solution of 2-chloro-3-cyano-6-methyl-isonicotinic acid ethyl ester (500 mg, 2.23 mmol) in EtOH (25 mL) at room temperature. The mixture was heated to reflux for 24 h. The mixture was cooled (crystallization began upon cooling) to room temperature. The solid was collected by vacuum filtration giving 3-cyano-2-mercapto-6-methyl-isonicotinic acid ethyl ester (250 mg, 50%) as a yellow orange solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. temperatureThe mixture was cooled
  4. custom(crystallization began upon cooling) to room temperature
  5. filtrationThe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-fba9c231c5ed4d80ba0adf2392f528f2
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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