Thionyl Chloride → HCID 86741632, compound

HRID 653159Notes

Reaction equation

HRID 653159 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6]2.[S:24](Cl)([Cl:26])=[O:25]>CCCCCCC>[Cl:26][S:24]([C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:25]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13295697Ethyl 1-benzyl-5-methoxy-1H-indole-2-carboxylate

Product 1

HCID 86741632HCID 86741632, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A suspension of 7.0 g (0.023 mole) of 5-methoxy-1-phenylmethyl-1H-indole-2-carboxylic acid, ethyl ester (Y. Murakami, et al, Synthesis, 738 (1984)) in 75 ml of n-heptane under an argon atmosphere was cooled in ice and treated with 15.0 ml (24.5 g; 0.21 mole) of thionyl chloride. The mixture was stirred for 30 minutes, and the precipitated sulfinyl chloride intermediate was filtered and washed several times with hexane to yield 7.3 g (76% yield) of 3-(chlorosulfinyl)-5-methoxy-1-phenylmethyl-1H-indole-2-carboxylic acid, ethyl ester.

Workup

  1. temperaturewas cooled in ice
  2. filtrationthe precipitated sulfinyl chloride intermediate was filtered
  3. washwashed several times with hexane

Sources & evidence

ORD record
ord-caf62a64e6404031b1fc74284d4fa371
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

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