Hexane → HCID 13837943, compound

HRID 653158Notes

Reaction equation

HRID 653158 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C:18]([O:20][CH3:21])=[O:19])=[CH:6]2.[S:22](Cl)([Cl:24])=[O:23].CCCCCC>CCOCC>[Cl:24][S:22]([C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[C:18]([O:20][CH3:21])=[O:19])=[O:23]

Participants

5

Reactant 3

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 13837942Methyl 5-methoxy-1-phenyl-1H-indole-2-carboxylate

Product 1

HCID 13837943HCID 13837943, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4.0 g (0.014 mole) of 5-methoxy-1-phenyl-1H-indole-2-carboxylic acid, methyl ester in 7.0 ml (11.4 g; 0.096 mole) of thionyl chloride (under a nitrogen atmosphere) was stirred at ambient temperature for ten minutes. After the addition of 50 ml of 20% hexane in ether solution, the new mixture was cooled in ice for 30 minutes to precipitate the crude intermediate sulfinyl chloride. The solid was filtered and washed with hexane to yield 3.0 g (63% crude yield) of 3-(chlorosulfinyl)-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid, methyl ester.

Workup

  1. temperaturethe new mixture was cooled in ice for 30 minutes
  2. customto precipitate the crude intermediate sulfinyl chloride
  3. filtrationThe solid was filtered
  4. washwashed with hexane

Sources & evidence

ORD record
ord-eed663eaa6d644d4bb363f4b50c81f78
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

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