Sulfuric Acid → HCID 20270201, compound

HRID 485362Notes

Reaction equation

HRID 485362 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:22]=1)(=O)=O.S(=O)(=O)(O)O>CN(C)C=O>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:20][C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)[CH:22]=2)=[CH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8434EthylparabenHCID 24758Sodium hydrideHCID 20270203HCID 20270203, compound

Product 1

HCID 20270201HCID 20270201, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4.55 g of ethyl p-hydroxybenzoate in 50 ml of dry dimethylformamide is treated with 1.31 g of 50% sodium hydride dispersion in mineral oil under nitrogen at 0°, stirred for 30 minutes at 0°, and then at room temperature for 15 minutes. A solution of 7.55 g of 3-(methanesulfonyloxymethyl)-N-(3-pyridyl)indole in 10 ml of dry dimethylformamide is added over 5 minutes and the reaction mixture is warmed at 50° for 18 hours. The reaction mixture is poured onto ice, made acidic with concentrated sulfuric acid and extracted with diethyl ether (4×40 ml). The aqueous phase is adjusted to pH=8 and is extracted with diethyl ether (3×100 ml). The organic extracts are washed with water (4×50 ml) and brine (1×50 ml) and dried over anhydrous sodium sulfate. Evaporation and chromatography on 100 g of silica with diethyl ether as the eluent yields 3-[(p-ethoxycarbonylphenoxy)methyl]-N-(3 -pyridyl)indole.

Workup

  1. waitat room temperature for 15 minutes
  2. temperaturethe reaction mixture is warmed at 50° for 18 hours
  3. additionThe reaction mixture is poured onto ice
  4. extractionextracted with diethyl ether (4×40 ml)
  5. extractionis extracted with diethyl ether (3×100 ml)
  6. washThe organic extracts are washed with water (4×50 ml) and brine (1×50 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customEvaporation and chromatography on 100 g of silica with diethyl ether as the eluent

Sources & evidence

ORD record
ord-7240b2d94f0e41f594fbbcfdd82ca7b0
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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