Hydrochloric Acid → HCID 178459369, compound

HRID 1449034Notes

Reaction equation

HRID 1449034 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 3 N 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 acetone-hexane 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-434e1e76d5a0492bb53206ffe46e9260
Source dataset
uspto-grants-1980_02
Patent number
US04188487

Reaction notes

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