Sodium methanethiolate → HCID 21905378, compound

HRID 1247324Notes

Reaction equation

HRID 1247324 reaction equation
[CH3:1][S-:2].[Na+].Br[CH:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1)=[O:7]>CO.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:6](=[O:7])[CH:5]([S:2][CH3:1])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][CH:12]=1)#[N:17]

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 21905686HCID 21905686, compound

Product 1

HCID 21905378HCID 21905378, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of sodium methanethiolate (0.43 g) at rt in methanol (15 ml) were added the (RS)-2-bromo-N-(4-cyano-benzyl)-2-phenyl-acetamide (0.5 g, example 81.1) and a catalytic amount of tetrabutyl ammonium iodide. The mixture was then stirred at rt for 1 hr. The mixture was concentrated. The residue was taken up in EtOAc, washed with 1.0 N and brine, dried over MgSO4, filtered and concentrated. The product was isolated by chromatography (silica gel, cyclohexane/EtOAc 2:1) to give (RS)-N-(4-cyano-benzyl)-2-methylsulfanyl-2-phenyl-acetamide (0.36 g). Colorless solid. MS 297.2 ([M+H]+)

Workup

  1. concentrationThe mixture was concentrated
  2. washwashed with 1.0 N and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was isolated by chromatography (silica gel, cyclohexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-15a8d625e0cc4d9f953bce66e9d85c95
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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