Methyl iodide → HCID 21270034, compound

HRID 1194360Notes

Reaction equation

HRID 1194360 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH3:19])=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[C:20](=O)([O-])[O-].[K+].[K+].IC>CS(C)=O.O>[N:1]1([CH2:6][CH2:7][C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH3:20])[C:11]=2[CH3:19])=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21270047HCID 21270047, compound

Product 1

HCID 21270034HCID 21270034, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(1H-imidazol-yl)-1-(2-methyl-1H-indol-3-yl)-1-propanone (148 mg), and potassium carbonate (0.7 g) in dimethylsulphoxide (5 ml) was stirred for 1 h and treated with iodomethane (0.10 g). The mixture was stirred for a further 4 h then diluted with water and extracted with ether (200 ml total). The combined organic extracts were washed with water, dried and evaporated to give the title compound which was crystallised from ethyl acetate to give a solid (80 mg), m.p. 151°-152°; λmax (EtOH) 246.5 nm (ε12,940), λmax 268.5 nm (ε8,740), λmax 306.5 nm (ε12,215).

Workup

  1. stirringThe mixture was stirred for a further 4 h
  2. extractionextracted with ether (200 ml total)
  3. washThe combined organic extracts were washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-3d6b15865d5548a7af57332cd4050351
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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