Phosphoric Acid → HCID 178487323, compound

HRID 2257963Notes

Reaction equation

HRID 2257963 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:11][CH2:12][C:13]([C:15]1[N:16]=[CH:17][NH:18][CH:19]=1)=O.P(=O)(O)(O)O.S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[C:4]2[C:5]([C:13]([C:15]3[N:16]=[CH:17][NH:18][CH:19]=3)=[CH:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178490109HCID 178490109, compound

Product 1

HCID 178487323HCID 178487323, compoundYield 46.1%

Procedure

5 g (0.0206 mole) of 3-(2,3-dimethoxyphenyl)-1-(1H-imidazol-4-yl)-1-propanone prepared in Example 2.4.a (and/or in Example 2.3.a) are stirred at room temperature for 16 hours in 100 ml of a 50:50 (v/v) mixture of 85% phosphoric acid and 95% sulphuric acid. The reaction medium is then poured onto ice, the mixture is brought to pH 7.5 by addition of an aqueous solution of sodium hydroxide cooled to a temperature of less than 10° C., and the mixture is then extracted with dichloromethane. The solvent is evaporated from the organic phase and the residue is treated by chromatography (stationary phase:silica; eluent: 95:5 (v/v) mixture of dichloromethane-methanol). 2.3 g of 4-(6,7-dimethoxy-1H-inden-3-yl)-1H-imidazole are obtained.

Workup

  1. additionThe reaction medium is then poured onto ice
  2. temperaturecooled to a temperature of less than 10° C.
  3. extractionthe mixture is then extracted with dichloromethane
  4. customThe solvent is evaporated from the organic phase
  5. additionthe residue is treated by chromatography (stationary phase:silica; eluent: 95:5 (v/v) mixture of dichloromethane-methanol)

Sources & evidence

ORD record
ord-0f67d242e7014f6a8d2f3d1468001ff0
Source dataset
uspto-grants-1997_08
Patent number
US05658938

Reaction notes

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