Methyl iodide → HCID 53932142, compound

HRID 1089818Notes

Reaction equation

HRID 1089818 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:6]([N+:24]([O-:26])=[O:25])=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])=[C:8]2[C:20]([O:22][CH3:23])=[O:21].[CH3:27]I.OS([O-])(=O)=O.[Na+]>CN(C)C=O>[CH3:3][O:4][C:5]1[C:6]([N+:24]([O-:26])=[O:25])=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:27])[C:9]([CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])=[C:8]2[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516919Sodium BisulfateHCID 54246507HCID 54246507, compound

Product 1

HCID 53932142HCID 53932142, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

This synthesis was carried out under an atmosphere of dry N2. To a stirred suspension of NaH (2.9 g) in dimethylformamide (145 ml) were added 9.34 g (28 mmol) methyl 5-methoxy-3-methoxycarbonyl-4-nitro-2-indoleacrylate (15). Thereupon the whole mixture was heated at 45°-50° C. When the evolution of H2 had ceased methyliodide (25 ml) was added to the dark red solution. During an additional (1 h) heating of the reaction mixture at 60° C., the colour of the solution turned to yellow. After cooling this mixture was poured into cold (0° C.) 10% NaHSO4 aq. Yellow crystals separated, which were collected by filtration, washed with water and ethanol, and finally dried in vacuo at 50°-60° C.

Workup

  1. temperatureThereupon the whole mixture was heated at 45°-50° C
  2. additionwas added to the dark red solution
  3. temperatureAfter cooling this mixture
  4. customseparated
  5. filtrationwhich were collected by filtration
  6. washwashed with water and ethanol
  7. customfinally dried in vacuo at 50°-60° C.

Sources & evidence

ORD record
ord-b124e1a6377a4535af65e59637d5960b
Source dataset
uspto-grants-1992_01
Patent number
US05079257

Reaction notes

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