Hydrochloric Acid → HCID 178482269, compound

HRID 620832Notes

Reaction equation

HRID 620832 reaction equation
[C:1]([N:4]([C:6]1[C:11]([Cl:12])=[CH:10][C:9]([C:13]2[NH:14][C:15]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[C:16]([CH3:18])[N:17]=2)=[C:8]([O:25][CH3:26])[CH:7]=1)C)(=O)C.Cl>O.C(O)C>[Cl:12][C:11]1[C:6]([NH:4][CH3:1])=[CH:7][C:8]([O:25][CH3:26])=[C:9]([C:13]2[NH:14][C:15]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[C:16]([CH3:18])[N:17]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178493182HCID 178493182, compound

Product 1

HCID 178482269HCID 178482269, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-[4-(N-acetyl-N-methylamino)-5-chloro-2-methoxyphenyl]-4-methyl-5-(3-pyridyl)imidazole (0.70 g) and conc. hydrochloric acid (7 ml) in a mixture of water (7 ml) and ethanol (7 ml) was refluxed for 7 hours with stirring. After allowed to cool to ambient temperature, the mixture was evaporated under reduced pressure. The resulting oil was poured into water (20 ml). After neutrallized with aqueous potassium bicarbonate the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was distilled off to give 2-(5-chloro-4-methylamino-2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (0.58 g).

Workup

  1. temperaturewas refluxed for 7 hours
  2. customthe mixture was evaporated under reduced pressure
  3. additionThe resulting oil was poured into water (20 ml)
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-3b417f06d3394f4b98ef49d695fb8ef1
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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