Methanol → 1-Benzenesulfonyl-5-methylthioindole-2-carboxylic acid methyl ester

HRID 1838356Notes

Reaction equation

HRID 1838356 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:20]([OH:22])=[S:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:28]O>>[CH3:28][O:22][C:20]([C:11]1[N:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])[C:18]2[C:13]([CH:12]=1)=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=2)=[S:21]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178422521HCID 178422521, compound

Product 1

HCID 865988551-Benzenesulfonyl-5-methylthioindole-2-carboxylic acid methyl ester

Procedure

A mixture of 1-benzenesulfonyl-5-methylthioindole-2-carboxylic acid (3.5 g), sulfuric acid (10 ml) and methanol (10 ml) was heated under reflux for 12 hours. The reaction mixture was poured into ice-water and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (dichloromethane) to obtain 3.4 g of the desired product as a white crystal.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55a315aa8530429b8affda0afab1f4f9
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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