Ethyl Thioglycolate → 3-[3-(ethoxycarbonylmethylthio)propyl]-N-(3-pyridyl)indole

HRID 485343Notes

Reaction equation

HRID 485343 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)[CH:11]=1.[C:25]1(S(OCCC)(=O)=O)[CH:30]=CC=C[CH:26]=1>CN(C)C=O.O>[CH2:6]([O:5][C:3]([CH2:2][S:1][CH2:26][CH2:25][CH2:30][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([C:12]2[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=2)[CH:17]=1)=[O:4])[CH3:7]

Participants

6

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 86740258N-(3-pyridyl)indole 3-propyl benzenesulfonate

Product 1

HCID 202701983-[3-(ethoxycarbonylmethylthio)propyl]-N-(3-pyridyl)indole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.36 g of ethyl mercaptoacetate in 20 ml of dimethylformamide is treated with 0.145 g of a 50% oil dispersion of sodium hydride at room temperature under nitrogen for 15 minutes. A solution of 1.13 g of N-(3-pyridyl)indole-3-propyl benzenesulfonate in 5 ml of dimethylformamide is added at room temperature. The reaction mixture is stirred for 15 hours, diluted with 100 ml of water and extracted 4 times with 50 ml of ethyl ether. The organic extracts are washed with 50 ml of water and 20 ml of cold 1N hydrochloric acid. The acid phase is extracted with ether and brought to pH=8.5 with 50% sodium hydroxide solution. The aqueous phase is extracted with chloroform (3×30 ml). The chloroform extract is dried over potassium carbonate and evaporated to yield 3-[3-(ethoxycarbonylmethylthio)propyl]-N-(3-pyridyl)indole; IR (CH2Cl2) 1725 cm-1.

Workup

  1. extractionextracted 4 times with 50 ml of ethyl ether
  2. washThe organic extracts are washed with 50 ml of water and 20 ml of cold 1N hydrochloric acid
  3. extractionThe acid phase is extracted with ether
  4. extractionThe aqueous phase is extracted with chloroform (3×30 ml)
  5. extractionThe chloroform extract
  6. dry with materialis dried over potassium carbonate
  7. customevaporated

Sources & evidence

ORD record
ord-521735bd8390406ea7297250b6ab968e
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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