Water → HCID 20532027, compound

HRID 1759440Notes

Reaction equation

HRID 1759440 reaction equation
C1(C)C=CC(S(O[CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[O:21])=[CH:16][CH:15]=2)[C:12]#[N:13])(=O)=O)=CC=1.[Na].[SH:29][C:30]1[S:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1.O>COCCOC>[S:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=[C:30]1[S:29][CH:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[O:21])=[CH:18][CH:19]=1)[C:12]#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 12945138HCID 12945138, compoundHCID 178418395HCID 178418395, compound

Product 1

HCID 20532027HCID 20532027, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.191 g of O-(p-toluenesulfonyl)-p-(2-thienylcarbonyl)mandelonitrile was dissolved in 5 ml of DME, and the solution was stirred in an argon atmosphere under ice cooling. Sodium salt of 2-mercaptobenzothiazole (567 mg) was added, and the mixture was stirred under ice cooling for 45 minutes, and then at room temperature for 30 minutes. Water (30 ml) was added, and the mixture was extracted with 30 ml of methylene chloride three times. The extract was washed with 20 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 788 mg (yield 67%) of alpha-(2-benzothiazolylthio)[p-(2-thienylcarbonyl)phenyl] acetonitrile as a viscous oil.

Workup

  1. stirringthe mixture was stirred under ice cooling for 45 minutes
  2. extractionthe mixture was extracted with 30 ml of methylene chloride three times
  3. washThe extract was washed with 20 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-e511dc11f80742e1ba1c140cb4536a61
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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