4-Methylbenzenethiol → HCID 12945141, compound

HRID 1759428Notes

Reaction equation

HRID 1759428 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.C[O-].[Na+].[C:31]1([CH3:38])[CH:36]=[CH:35][C:34]([SH:37])=[CH:33][CH:32]=1.[Cl-].[NH4+]>CN(C=O)C.CO>[C:31]1([CH3:38])[CH:36]=[CH:35][C:34]([S:37][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[O:21])=[CH:18][CH:19]=2)[C:12]#[N:13])=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 78114-MethylbenzenethiolHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 12945138HCID 12945138, compound

Product 1

HCID 12945141HCID 12945141, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
-15 °C

Procedure

795 mg of O-(p-toluenesulfonyl)-p-(2-thienylcarbonyl)mandelonitrile was dissolved in 3 ml of anhydrous DMF, and the solution was stirred at -15° C. in an argon atmosphere. A solution prepared by adding 0.80 ml of a 2.5 M methanol solution of sodium methoxide at room temperature to 2 ml of an anhydrous methanol solution containing 250 mg of p-toluenethiol was added dropwise over the course of 10 minutes. After the addition, the mixture was further stirred, and its temperature was gradually raised to bring it to -5° C. in 20 minutes. At this time, an aqueous solution of ammonium chloride (1 g/30 ml) was added to the reaction mixture, and the mixture was extracted with 20 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 recrystallized from ethanol to afford 387 mg of alpha-[p-tolylthio)[p-(2-thienylcarbonyl)phenyl]acetonitrile as colorless crystals. The mother liquor was concentrated under reduced pressure, and the residue was separated by column chromatography (silica gel; methylene chloride) to afford 95 mg of alpha(p-tolylthio)[p-(2-thienylcarbonyl)phenyl]acetonitrile. The total amount of the products yielded was 482 mg, and the yield was 69%.

Workup

  1. customA solution prepared
  2. additionwas added dropwise over the course of 10 minutes
  3. additionAfter the addition
  4. stirringthe mixture was further stirred
  5. temperatureits temperature was gradually raised
  6. customto -5° C.
  7. customin 20 minutes
  8. extractionthe mixture was extracted with 20 ml of methylene chloride three times
  9. washThe extract was washed with 20 ml of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c9dab49d193f4ac98909cde3d7ee1064
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

Loading…