Hydrochloric Acid → HCID 54278836, compound

HRID 1741602Notes

Reaction equation

HRID 1741602 reaction equation
[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:19]=[CH:18][C:17]([CH:20]=[CH:21][CH3:22])=[CH:16][C:11]=2[C:12]([O:14]C)=[O:13])=[N:5]1)([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[CH:1]([C:4]1([CH3:23])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:19]=[CH:18][C:17]([CH:20]=[CH:21][CH3:22])=[CH:16][C:11]=2[C:12]([OH:14])=[O:13])=[N:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54120843HCID 54120843, compound

Product 1

HCID 54278836HCID 54278836, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.5 g methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-propenylnicotinate and 3.2 mL of 2N sodium hydroxide in 15 mL methanol is stirred under nitrogen and heated at 45° for 31/2 hours. The reaction is cooled to 10°, acidified to pH 3 with 2N hydrochloric acid, and concentrated in vacuo. The residue is partitioned between methylene chloride and water, and the aqueous phase is further extracted with methylene chloride. The combined organic phases are dried and concentrated in vacuo to a solid. Recrystallization from methylene chloride-hexanes gives a solid, mp 175°-176°.

Workup

  1. temperatureheated at 45° for 31/2 hours
  2. temperatureThe reaction is cooled to 10°
  3. concentrationconcentrated in vacuo
  4. customThe residue is partitioned between methylene chloride and water
  5. extractionthe aqueous phase is further extracted with methylene chloride
  6. customThe combined organic phases are dried
  7. concentrationconcentrated in vacuo to a solid
  8. customRecrystallization from methylene chloride-hexanes
  9. customgives a solid, mp 175°-176°

Sources & evidence

ORD record
ord-e15a9f11cc0c46158a012fdf261e871d
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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