Methanol → alpha-(2-Benzothiazolylthio)(m-benzoylphenyl)-acetonitrile

HRID 1759437Notes

Reaction equation

HRID 1759437 reaction equation
CO.C1(C)C=CC(S(O[CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:17]=2)[C:14]#[N:15])(=O)=O)=CC=1.[Na].[SH:32][C:33]1[S:34][C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=1>O.COCCOC>[S:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=[C:33]1[S:32][CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:17]=1)[C:14]#[N:15]

Participants

7

Reactant 4

HCID 887MethanolHCID 5360545SodiumHCID 12945137O-(p-toluenesulfonyl)-m-benzoylmandelonitrileHCID 178418395HCID 178418395, compound

Product 1

HCID 20532028alpha-(2-Benzothiazolylthio)(m-benzoylphenyl)-acetonitrileYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Methanol (6 ml) and 3 ml of DME were added to 1.18 g of O-(p-toluenesulfonyl)-m-benzoylmandelonitrile, and the mixture was stirred in an argon atmosphere under ice cooling. Sodium salt of 2-mercaptobenzothiazole (570 mg) was added, and the mixture was stirred for 1.5 hours under ice cooling. Water (50 ml) was added, and the mixture was extracted with 30 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; methylene chloride) to afford 972 mg (yield 83%) of alpha-(2-benzothiazolylthio)-(m-benzoylphenyl)acetonitrile as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred for 1.5 hours under ice cooling
  2. extractionthe mixture was extracted with 30 ml of methylene chloride three times
  3. washThe extract was washed with 40 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; methylene chloride)

Sources & evidence

ORD record
ord-0a9a5c045719438984471800f79025f1
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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