Hydrochloric Acid → HCID 178496783, compound

HRID 1770200Notes

Reaction equation

HRID 1770200 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 AcidHCID 887MethanolHCID 178509731HCID 178509731, compound

Product 1

HCID 178496783HCID 178496783, compound

Conditions

Temperature
5 °C

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 400 ml of methanol is cooled to -45° C. and saturated with gaseous hydrochloric acid. The suspension is allowed to return to 10° C. and gaseous hydrochloric acid is bubbled through the suspension for 4 hours more at that temperature. The suspension is cooled to 5° C. and kept at that temperature for 20 hours. The precipitate which has formed is filtered off and 11.4 g of methyl 2-hydroxy-3-(1H-imidazol-4-ylmethyl)-benzenecarboximidate are obtained in the form of a white solid which is used as such in the following step.

Workup

  1. customto return to 10° C.
  2. customgaseous hydrochloric acid is bubbled through the suspension for 4 hours more at that temperature
  3. customThe precipitate which has formed
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-46922b74f13b45c7ba6f494055bf58bd
Source dataset
uspto-grants-1995_01
Patent number
US05385927

Reaction notes

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