Water → HCID 59305848, compound

HRID 2240919Notes

Reaction equation

HRID 2240919 reaction equation
[CH3:1][O-].[Na+].[OH:4][N:5]1[C:9](=[O:10])[CH2:8][CH2:7][C:6]1=[O:11].C[C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[NH:16].O>CO>[O:11]=[C:6]1[CH2:7][CH2:8][C:9](=[O:10])[N:5]1[O:4][C:15](=[N:16][CH3:1])[C:14]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80170N-HydroxysuccinimideHCID 10942334Sodium MethoxideHCID 57361558HCID 57361558, compound

Product 1

HCID 59305848HCID 59305848, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.7 g (0.03 mol) of sodium methylate are added to a solution of 3.45 g (0.03 mol) of N-hydroxy succinimide in 25 ml of methanol. The reaction mixture is stirred for one h, concentrated under vacuo and the residue is taken up in 15 ml of DMF. 4.6 g (0.03 mol) of methyl benzimidoyl chloride are added on stirring. The reaction mixture is stirred at room temperature for 12 h and then poured into 120 ml of water. The so formed precipitate is sucked off and dried in vacuo to obtain 3.8 g of a crude product which is then taken up and recrystallised in 9 ml of toluene to give 3.05 g of N-methyl-benzimidic acid 2,5-dioxopyrrolidine-1-yl ester in form of colorless crystals; mp. 119-120° C.

Workup

  1. concentrationconcentrated under vacuo
  2. stirringon stirring
  3. stirringThe reaction mixture is stirred at room temperature for 12 h
  4. customThe so formed precipitate
  5. customdried in vacuo
  6. customto obtain 3.8 g of a crude product which
  7. customrecrystallised in 9 ml of toluene

Sources & evidence

ORD record
ord-42a56f7c7d004bfb8883d0bde78a73d3
Source dataset
uspto-grants-2010_05
Patent number
US07723399B2

Reaction notes

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