Sodium hydride → HCID 13362111, compound

HRID 1633135Notes

Reaction equation

HRID 1633135 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)[CH3:2].[H-].[Na+].CS(O[CH2:20][CH2:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH3:31])=[C:23]1[C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)(=O)=O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:20][CH2:21][N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([CH3:31])=[C:23]2[C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[CH:7][CH:6]=1)=[O:12])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10845149ethyl 4-mercaptobenzoateHCID 20441667HCID 20441667, compound

Product 1

HCID 13362111HCID 13362111, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5.9 g of p-mercaptobenzoic acid ethyl ester (prepared according to the procedure found in J. Chem. Soc., 1963, 1947-1954) in 30 ml of dimethylformamide is added dropwise to a slurry of 1.55 g of 50% sodium hydride (dispersion in mineral oil in 30 ml of dimethylformamide. This mixture is stirred at room temperature for 0.5 hour under nitrogen atmosphere. This solution is added dropwise to a solution of 9.78 g of 1-(2-methylsulfonyloxyethyl)-2-(3-pyridyl)-3-methylindole in 60 ml of dimethylformamide at -10°. This mixture is stirred at room temperature overnight and poured into 1 liter of ice-water. This is extracted several times with ether (ca 1 liter total). The ether extract is washed with water (3×200 ml), dried over MgSO4 and evaporated in vacuo yielding 1-[2-(4-ethoxycarbonylphenylthio)ethyl]-2-(3-pyridyl)-3-methylindole as an oil; NMR (CDCl3) confirms the structure.

Workup

  1. stirringThis mixture is stirred at room temperature overnight
  2. extractionThis is extracted several times with ether (ca 1 liter total)
  3. extractionThe ether extract
  4. washis washed with water (3×200 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8a471336d16a462abed5eb9b4fae2808
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

Loading…