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Methyl iodide → alpha-(2-Benzothiazolylthio)-alpha-(m-benzoylphenyl)propionitrile

HRID 1759438
Notes
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Reaction equation

HRID 1759438 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1)[C:12]#[N:13].[CH3:28][O-].[Na+].CI.[Cl-].[NH4+]>CO.COCCOC>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:15]=1)([CH3:28])[C:12]#[N:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 20532028alpha-(2-Benzothiazolylthio)(m-benzoylphenyl)-acetonitrile

Product 1

HCID 54504093alpha-(2-Benzothiazolylthio)-alpha-(m-benzoylphenyl)propionitrileYield 70%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
2×
HCID 80711,2-DimethoxyethaneSolvent

Procedure

Methanol (3 ml) and 2 ml of DME were added to 802 mg of alpha-(2-benzothiazolylthio)(m-benzoylphenyl)-acetonitrile, and the mixture was stirred in an argon atmosphere under ice cooling. Then, 0.78 ml of a 2.7 M methanol solution of sodium methoxide was added, and then 0.19 ml of methyl iodide was added dropwise. The reaction mixture was stirred at room temperature for 1 hour, and after adding an aqueous solution of ammonium chloride (1 g/20 ml), extracted with 40 ml of methylene chloride three times. The extract was washed with 50 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (silica gel; benzene and methylene chloride) to afford 580 mg (yield 70%) of alpha-(2-benzothiazolylthio)-alpha-(m-benzoylphenyl)propionitrile as an oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. extractionextracted with 40 ml of methylene chloride three times
  3. washThe extract was washed with 50 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated by column chromatography (silica gel; benzene and methylene chloride)

Sources & evidence

ORD record
ord-dc1489186b304df1b7bcbef476ea8cf6
Source dataset
uspto-grants-1982_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04340740

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes