Hydrochloric Acid → HCID 178496783, compound
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.[OH2:17].[CH3:18]O>>[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:17][CH3:18]Participants
Conditions
- Temperature
- 10 °C
Procedure
A suspension of 19.9 g (0.1 mole) of 2-hydroxy-3-(1H-imidazol-4-ylmethyl)-benzonitrile (prepared in example 1.1 above) in 600 ml of methanol, cooled to 10° C., is saturated with gaseous hydrochloric acid. 60 ml of water are added, the suspension is cooled to -25° C. and is saturated once again with gaseous hydrochloric acid. The reaction mixture is kept at that temperature for 15 hours. The solution is evaporated and the residue is taken up in 500 ml of ice-cold water; the resulting suspension is neutralized with an aqueous sodium bicarbonate solution. The solution is extracted 4 times with 250 ml of ethyl acetate and the organic phases are combined. The organic phase is washed with 200 ml of a saturated aqueous sodium chloride solution, is then dried over magnesium sulfate, filtered and evaporated. 19.1 g of methyl 2-hydroxy-3-(1H-imidazol-4-ylmethyl-)benzenecarboximidate are obtained which are used as such in the following step.
Workup
- temperaturethe suspension is cooled to -25° C.
- customThe solution is evaporated
- extractionThe solution is extracted 4 times with 250 ml of ethyl acetate
- washThe organic phase is washed with 200 ml of a saturated aqueous sodium chloride solution
- dry with materialis then dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-2d2a1bd63eea4cb09d4b37f4cb52f517
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05385927
Reaction notes
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