Hydrochloric Acid → HCID 178498876, compound

HRID 235926Notes

Reaction equation

HRID 235926 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:24])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:17][CH:18]=[C:19]([C:21]([OH:23])=[O:22])[N:20]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:26]O>>[C:1]([NH:5][CH2:6][CH:7]([OH:24])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:17][CH:18]=[C:19]([C:21]([O:23][CH3:26])=[O:22])[N:20]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178449127HCID 178449127, compound

Product 1

HCID 178498876HCID 178498876, compound

Procedure

A solution of crude 2-[4-(3-tert-butylamino-2-hydroxypropoxy)phenyl]-4-carboxyimidazole ◯1 (30 g.) in methanol (600 ml.) is heated to reflux, and then heating is discontinued as hydrogen chloride is bubbled rapidly through the solution with stirring for a half hour, followed by two and a half hours at reflux. Bubbling of hydrogen chloride is continued for another two hours followed by another hour at reflux and then the reaction mixture is stirred at room temperature overnight. The mixture is filtered and the filtrate is then concentrated to dryness under reduced pressure. The residue is dissolved in water (150 ml.) and the pH is adjusted to 8 with saturated sodium carbonate solution. The basic mixture is extracted with ethyl acetate and the extracts are dried, filtered, and concentrated under reduced pressure to yield a solid which is recrystallized from acetonitrile to yield the methyl 2-[4-(3-tert. butylamino-2-hydroxypropoxy)phenyl]-imidazole-4-carboxylate as a cream-colored solid, m.p. 168°-172° C.

Workup

  1. temperatureto reflux
  2. temperatureheating
  3. customis bubbled rapidly through the solution
  4. waitfollowed by two and a half hours
  5. temperatureat reflux
  6. customBubbling of hydrogen chloride
  7. waitfollowed by another hour
  8. temperatureat reflux
  9. stirringthe reaction mixture is stirred at room temperature overnight
  10. filtrationThe mixture is filtered
  11. concentrationthe filtrate is then concentrated to dryness under reduced pressure
  12. dissolutionThe residue is dissolved in water (150 ml.)
  13. extractionThe basic mixture is extracted with ethyl acetate
  14. customthe extracts are dried
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure
  17. customto yield a solid which
  18. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-cd47bac3375f4ba1b1d658bf34431be1
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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