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

HRID 1759439Notes

Reaction equation

HRID 1759439 reaction equation
C1(C)C=CC(S(O[CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:15]=2)[C:12]#[N:13])(=O)=O)=CC=1.[Na].[SH:30][C:31]1[S:32][C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=1.[CH3:40][O-].[Na+].CI.[Cl-].[NH4+]>CO.COCCOC>[S:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=[C:31]1[S:30][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)([CH3:40])[C:12]#[N:13]

Participants

9

Reactant 6

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 12945137O-(p-toluenesulfonyl)-m-benzoylmandelonitrileHCID 178418395HCID 178418395, compound

Product 1

HCID 54504093alpha-(2-Benzothiazolylthio)-alpha-(m-benzoylphenyl)propionitrileYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.18 g of O-(p-toluenesulfonyl)-m-benzoylmandelonitrile was dissolved in a mixture of 4 ml of methanol and 3 ml of DME, and the solution was stirred in an argon atmosphere under ice cooling. Sodium salt of 2-mercaptobenzothiazole (570 mg) was addded, and the mixture was stirred for 1 hour under ice cooling. Then, 1.15 ml of a 2.7 M methanol solution of sodium methoxide was added, and 0.22 ml of methyl iodide was further added dropwise. The temperature was brought to room temperature, and the solution was stirred for 1 hour. An aqueous solution of ammonium chloride (1 g/20 ml) was added, and the mixture was extracted with 40 ml of methylene chloride three times. The extract was washed with 40 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 892 mg (yield 74%) of alpha-(2-benzothiazolyl-thio)-alpha-(m-benzoylphenyl)propionitrile.

Workup

  1. stirringthe mixture was stirred for 1 hour under ice cooling
  2. customwas brought to room temperature
  3. stirringthe solution was stirred for 1 hour
  4. extractionthe mixture was extracted with 40 ml of methylene chloride three times
  5. washThe extract was washed with 40 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was separated by column chromatography (silica gel; benzene and methylene chloride)

Sources & evidence

ORD record
ord-b5fedf6d1dcb458e9ad2dfa22500cfe1
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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