Hydrochloric Acid → HCID 23043790, compound

HRID 2165117Notes

Reaction equation

HRID 2165117 reaction equation
[ClH:1].CN([CH2:5][CH:6]1[CH2:18][CH2:17][C:9]2[O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:8]=2[C:7]1=[O:19])C.[CH3:20][C:21]1[NH:22][CH:23]=[CH:24][N:25]=1.Cl>O>[ClH:1].[CH3:20][C:21]1[N:22]([CH2:5][CH:6]2[CH2:18][CH2:17][C:9]3[O:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:8]=3[C:7]2=[O:19])[CH:23]=[CH:24][N:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 127492-MethylimidazoleHCID 23043784HCID 23043784, compound

Product 1

HCID 23043790HCID 23043790, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 2-[(dimethylamino)methyl]-3,4-dihydro-1(2H)-dibenzofuranone hydrochloride (1.00 g), 2-methylimidazole (1.47 g) and water (25 ml) was heated under reflux for 20 h. The cooled mixture was acidified to pH 1 with aqueous 2M hydrochloric acid and extracted with ethyl acetate (2×50 ml; discarded). The aqueous layer was basified to pH 8 with aqueous saturated sodium bicarbonate, extracted with ethyl acetate (5×40 ml), and the combined organic extracts were washed with water (50 ml). The organic layer was dried and evaporated, and the residue was crystallised from ethyl acetate to give the free base of the title compound (176 mg). Evaporation of the mother liquors afforded a further quantity of the free base of the title compound (370 mg). A portion of this solid (166 mg) was treated with ethyl acetate (40 ml), filtered, and concentrated to ca. 10 ml. The solution was acidified to pH 1 by the addition of ethanolic hydrogen chloride, and the precipitate was collected to give the title compound (171 mg), m.p. 217°-222°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. extractionextracted with ethyl acetate (2×50 ml; discarded)
  4. extractionextracted with ethyl acetate (5×40 ml)
  5. washthe combined organic extracts were washed with water (50 ml)
  6. customThe organic layer was dried
  7. customevaporated
  8. customthe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-919c96956aa1405a9fd24be19de89d58
Source dataset
uspto-grants-1990_07
Patent number
US04939144

Reaction notes

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