Hydrochloric Acid → HCID 178496783, compound

HRID 1770199Notes

Reaction equation

HRID 1770199 reaction equation
[OH:1][C:2]1[C:9]([CH2:10][C:11]2[N:12]=[CH:13][NH:14][CH:15]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[CH3:17][OH:18]>>[OH:1][C:2]1[C:9]([CH2:10][C:11]2[N:12]=[CH:13][NH:14][CH:15]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[C:4](=[NH:5])[O:18][CH3:17]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 178509731HCID 178509731, compound

Product 1

HCID 178496783HCID 178496783, compound

Procedure

A suspension of 14.1 g (0.071 mole) of 2-hydroxy-3-(1H-imidazol-4-ylmethyl)-benzonitrile (prepared in example 1.1 above) in 420 ml of methanol is cooled to -40° C. and saturated with gaseous hydrochloric acid. The suspension is allowed to return to 10° C. and is saturated once again with gaseous hydrochloric acid. The reaction mixture is kept at that temperature for 20 hours. The solution is concentrated to 200 ml, 300 ml of ice-cold water and 300 ml of ethyl acetate are added to the concentrated solution and the solution is then neutralized using an aqueous sodium bicarbonate solution. The solution is filtered, and the aqueous phase is separated from the organic phase, then the aqueous phase is extracted twice with 300 ml of ethyl acetate and the organic phases are combined. The organic phase is washed with a saturated aqueous sodium chloride solution, is then dried over magnesium sulfate, filtered and evaporated under reduced pressure. 15.4 g of methyl 2-hydroxy-3-(1H-imidazol- 4-ylmethyl)-benzenecarboximidate are obtained as a beige solid product which is taken up in 210 ml of absolute ethanol.

Workup

  1. customto return to 10° C.
  2. concentrationThe solution is concentrated to 200 ml, 300 ml of ice-cold water and 300 ml of ethyl acetate
  3. additionare added to the concentrated solution
  4. filtrationThe solution is filtered
  5. customthe aqueous phase is separated from the organic phase
  6. extractionthe aqueous phase is extracted twice with 300 ml of ethyl acetate
  7. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  8. dry with materialis then dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4a6702e2d88942b6946431443b336692
Source dataset
uspto-grants-1995_01
Patent number
US05385927

Reaction notes

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