Acetonitrile → HCID 14991366, compound

HRID 1195819Notes

Reaction equation

HRID 1195819 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[CH3:14][S-:15].[Na+].C(#N)C>O>[CH3:13][C:4]1[CH:3]=[C:2]([S:15][CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2342754-chloro-2,6-dimethylquinolineHCID 4378561Sodium methanethiolate

Product 1

HCID 14991366HCID 14991366, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-2,6-dimethylquinoline (0.5 g, prepared as described in Example 1), sodium thiomethoxide (0.55 g) and dry acetonitrile (20 ml) was heated to reflux under an atmosphere of argon for 15 hours. After cooling to laboratory temperature the mixture was poured into water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were dried over magnesium sulphate and evaporated to leave 2,6-dimethyl-4methylthioquinoline as a white solid (0.52 g) which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under an atmosphere of argon for 15 hours
  3. temperatureAfter cooling to laboratory temperature the mixture
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-c296313bf6ac4033bb08018ebbb1a207
Source dataset
uspto-grants-1992_05
Patent number
US05112837

Reaction notes

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