Water → 2-(1-methyl-1H-imidazol-2-ylmethyl)-isoindol-1,3-dione

HRID 2080754Notes

Reaction equation

HRID 2080754 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]([CH3:9])[CH:6]=[CH:7][N:8]=1.CC(C)([O-])C.[Na+].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K].O>CN(C=O)C>[CH3:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[CH2:3][N:20]1[C:16](=[O:26])[C:17]2[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:19]1=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 27954062-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 23676156Sodium t-butoxideHCID 24194345Phthalimide potassium salt

Product 1

HCID 231554212-(1-methyl-1H-imidazol-2-ylmethyl)-isoindol-1,3-dioneYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The compound (83.50 g) obtained in Example 10-2 was suspended in DMF (250 ml) and added with sodium t-butoxide (49.00 g) at −30° C. The solution was further added with a potassium phthalimide salt (95.0 g) and then the whole was stirred at 70° C. for 2 hours. After completion of the reaction, the resultant was added into water (800 ml). The precipitated crystal was filtrated, washed with water, and dried, thereby obtaining the subject compound (101.5 g) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationThe precipitated crystal was filtrated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-939b6bbf0f5a4400919cd7731713f4de
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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