Sodium Methoxide → HCID 11035035, compound

HRID 1075411Notes

Reaction equation

HRID 1075411 reaction equation
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:3](=[C:4]23)[CH:2]=1.[CH3:26][O-].[Na+]>C(O)C>[CH3:26][N:22]1[C:21](=[O:25])[C:5]2[C:4]3[C:19]4[C:8](=[CH:7][CH:6]=2)[C:9]2[C:20]5[C:13]([CH:12]=[CH:11][CH:10]=2)=[CH:14][CH:15]=[CH:16][C:17]=5[C:18]=4[CH:1]=[CH:2][C:3]=3[C:23]1=[O:24]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 11759047Perylene-3,4-dicarboximide

Product 1

HCID 11035035HCID 11035035, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.29 g (4 mmol) of perylene-3,4-dicarboximide and 0.56 g (14.7 mmol) of sodium methylate are suspended in 50 ml of ethanol and the mixture is stirred for 5 h at room temperature. After removing the solvent by evaporation under reduced pressure, 50 ml of N-methyl-pyrrolidone and 1.01 ml of methyl iodide are added and the mixture is stirred for 2 h at room temperature. The solvent is removed by distillation under reduced pressure and the residue is washed with 100 ml of sulfuric acid (20%) and is then collected by suction and dried at 130° C. under reduced pressure, giving 1.17 g (87%) of red N-methylperylene-3,4-dicarboximide. IR (KBr): ν=1692 cm-1 (s), 1657 (s), 1570 (s), 1361 (s), 1238 (m), 810 (s), 748 (m). C23H13O2N (335,36) cacld.: C 82.37 H 3.91 N 4.18 found: C 81.71 H 4.01 N 3.98

Workup

  1. customAfter removing the solvent
  2. customby evaporation under reduced pressure, 50 ml of N-methyl-pyrrolidone and 1.01 ml of methyl iodide
  3. additionare added
  4. stirringthe mixture is stirred for 2 h at room temperature
  5. customThe solvent is removed by distillation under reduced pressure
  6. washthe residue is washed with 100 ml of sulfuric acid (20%)
  7. customis then collected by suction
  8. customdried at 130° C. under reduced pressure

Sources & evidence

ORD record
ord-ac3b69c5e99c4265882ff5048d2e87db
Source dataset
uspto-grants-1999_05
Patent number
US05900490

Reaction notes

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