Hydrochloric Acid → HCID 10542363, compound

HRID 21580Notes

Reaction equation

HRID 21580 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH3:15])=[O:13])=[CH:6]2.[CH3:16][S:17]([CH3:19])=O.[ClH:20]>CO>[Cl-:20].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH3:15])=[O:13])=[C:6]2[S+:17]([CH3:19])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 679Dimethyl SulfoxideHCID 27281841H-Indole-2-carboxylic acid, 5-methoxy-, methyl ester

Product 1

HCID 10542363HCID 10542363, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 5-methoxy-1H-indole-2-carboxylate (8.3 g, 40 mmol; Blaikie KG, Perkin WH Jr, J. Chem. Soc. 1924;125:296) and dimethyl sulfoxide (4.0 mL, 4.4 g, 56 mmol) in 75 mL of methanol is cooled in ice and treated with gaseous HCl. The temperature of the reaction mixture increases to 45° C. as the HCl is added. Additional HCl is added intermittently and the rate of cooling is adjusted so that a reaction temperature of 40°-50° C. is maintained for 3 hours. The mixture is cooled and the precipitated solid filtered and washed with ether to yield 6.3 g (52%) of [5-methoxy-2-(methoxycarbonyl)-1H-indol-3-yl] dimethylsulfonium chloride suitable for further synthesis; mp 130° C.-dec.

Workup

  1. temperatureis cooled in ice
  2. additionis added
  3. temperaturethe rate of cooling
  4. customis adjusted so that a reaction temperature of 40°-50° C.
  5. temperatureis maintained for 3 hours
  6. temperatureThe mixture is cooled
  7. filtrationthe precipitated solid filtered
  8. washwashed with ether

Sources & evidence

ORD record
ord-6f015bcee68545a8a8caebae396ee2f2
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Reaction notes

Loading…