Hydrochloric Acid → HCID 178459369, compound

HRID 426541Notes

Reaction equation

HRID 426541 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[H-].[Na+].[Na].[CH:8]([C:11]1([CH3:25])[N:15]2[C:16](=[O:23])[C:17]3[C:22]([C:14]2=[N:13][C:12]1=[O:24])=[CH:21][CH:20]=[CH:19][CH:18]=3)([CH3:10])[CH3:9].Cl>C(Cl)Cl>[CH:8]([C:11]1([CH3:25])[NH:15][C:14]([C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]([O:4][CH2:1][C:2]#[CH:3])=[O:23])=[N:13][C:12]1=[O:24])([CH3:10])[CH3:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7859Propargyl alcohol2×HCID 24758Sodium hydride2×HCID 27292473-isopropyl-3-methyl-3H-imidazo[2,1-a]isoindole-2,5-dioneHCID 5360545Sodium

Product 1

HCID 178459369HCID 178459369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To 12.5 ml of propargyl alcohol is added 0.1 g of a 50% suspension of sodium hydride in mineral oil. The addition is made under a blanket of nitrogen while the mixture is stirred and the temperature thereof maintained at from 20° C. to 25° C. by means of external cooling. The formation of the sodium salt of propargyl alcohol is complete in about 1 to 2 hours. To this solution is added 5.0 g of 3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole-2(3H),5-dione and the mixture stirred at room temperature overnight under a blanket of nitrogen. Thin layer chromatography indicates incomplete reaction and an additional 50 mg of a 50% suspension of sodium hydride in oil is added to the reaction mixture. After stirring overnight, the mixture is cooled to 5° C. and 0.7 ml of 3N hydrochloric acid is added. The mixture is then diluted with methylene chloride, washed with water and the organic phase dried and concentrated in vacuo. The crystalline residue is transferred to a filter funnel with hexane and air dried to give 6.02 g of 2-propynyl o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)benzoate, melting point 131°-144° C. Material from a similar reaction was recrystallized from acetonehexane to give pure product melting point 145°-147° C.

Workup

  1. additionThe addition
  2. temperaturethe temperature thereof maintained at from 20° C. to 25° C. by means of external cooling
  3. stirringthe mixture stirred at room temperature overnight under a blanket of nitrogen
  4. customreaction
  5. stirringAfter stirring overnight
  6. washwashed with water
  7. customthe organic phase dried
  8. concentrationconcentrated in vacuo
  9. customThe crystalline residue is transferred to a filter funnel with hexane and air
  10. customdried

Sources & evidence

ORD record
ord-4417b6cf6eb34511b5ed8eb1e0d3dd7e
Source dataset
uspto-grants-1979_10
Patent number
US04170462

Reaction notes

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