Methanol → alpha-(2-Benzothiazolylthio)-alpha-(m-phenoxyphenyl)propionitrile

HRID 1759443Notes

Reaction equation

HRID 1759443 reaction equation
[CH3:1]O.[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[S:12][CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1)[C:14]#[N:15].C[O-].[Na+].CI>O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[S:12][C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=1)([CH3:1])[C:14]#[N:15]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 20532030alpha-(2-Benzothiazolylthio)(m-phenoxyphenyl)acetonitrile

Product 1

HCID 54026807alpha-(2-Benzothiazolylthio)-alpha-(m-phenoxyphenyl)propionitrileYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanol (5 ml) was added to 945 mg of alpha-(2-benzothiazolylthio)(m-phenoxyphenyl)acetonitrile, and the mixture was stirred under ice cooling in an argon atmosphere. Then, 1.0 ml of a 2.7 M methanol solution of sodium methoxide was added, and the mixture was stirred under ice cooling for 10 minutes. Methyl iodide (0.25 ml) was then added. The mixture was stirred under ice cooling for 30 minutes, and then at room temperature for 2.5 hours. Then, 30 ml of water was added, and the reaction mixture was extracted with 20 ml of methylene chloride three times. The extract was washed with 10 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; benzene and methylene chloride) to afford 752 mg (yield 77%) of alpha-(2-benzothiazolylthio)-alpha-(m-phenoxyphenyl)propionitrile as an oil.

Workup

  1. stirringthe mixture was stirred under ice cooling for 10 minutes
  2. stirringThe mixture was stirred under ice cooling for 30 minutes
  3. extractionthe reaction mixture was extracted with 20 ml of methylene chloride three times
  4. washThe extract was washed with 10 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel; benzene and methylene chloride)

Sources & evidence

ORD record
ord-866a5ed2e4384f828861e7bd29f4e2f9
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

Loading…