Acetonitrile → HCID 18989226, compound

HRID 2395565Notes

Reaction equation

HRID 2395565 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=2[CH:5]=[CH:4]1.C(#N)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>O.CO>[CH3:19][S:20]([N:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=2[CH:5]=[CH:4]1)(=[O:22])=[O:21]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 2733668methyl 1H-indole-4-carboxylate

Product 1

HCID 18989226HCID 18989226, compoundYield 118.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydride (1.1 g of a 80% dispersion in mineral oil), methyl 1H-indole 4-carboxylate (5.46 g) and anhydrous acetonitrile were mixed under an inert atmosphere at 0° C. and stirred at room temperature for an hour. Methanesulphonyl chloride (1.8 g) was added at 0° C. and the mixture stirred at room temperature for 18 hours. Methanol and then water were then added and the mixture extracted with dichloromethane. The organic phase was washed with 2N hydrochloric acid, water, 1M sodium carbonate and water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by column chromatography eluting with ethyl acetate/hexane obtaining methyl 1-(methylsulphonyl)indole-4-carboxylate (4.7 g) as a white solid, m.p. 102°-104° C.

Workup

  1. stirringthe mixture stirred at room temperature for 18 hours
  2. extractionthe mixture extracted with dichloromethane
  3. washThe organic phase was washed with 2N hydrochloric acid, water, 1M sodium carbonate and water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-e47cbcccd5cd4a298ad6d46ea435bbca
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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