Methyl iodide → HCID 13518854, compound

HRID 370538Notes

Reaction equation

HRID 370538 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:20])[CH2:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:10][CH:9]=1.[CH2:21](I)[CH3:22].[CH3:24]I>CN(C)C=O>[CH3:3][O:4][C:5](=[O:20])[C:6]([CH2:21][CH3:22])([CH3:24])[C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6340IodoethaneHCID 24758Sodium hydride2×HCID 13059430HCID 13059430, compound

Product 1

HCID 13518854HCID 13518854, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Procedure

To a slurry of 2.49 g of sodium hydride (60% dispersion in Nujol) in 50 ml of dimethylformamide is added a solution of 24.4 g of 4-(1H-imidazol-1-yl)-β-oxobenzenepropanoic acid methyl ester in 75 ml of dimethylformamide at 15°-20° C. After the addition is completed 15.6 g of ethyl iodide is added and stirring is continued for 48 hours. The reaction mixture is filtered, poured into water, and the mixture is extracted with ether. Removal of the solvent and trituration with isopropyl ether gives an oil. A solution of 2.72 g of the oil in 10 ml of dimethylformamide is added to a slurry of 0.24 g of sodium hydride (60% dispersion in Nujol) at 15°-20°. A solution of 1.42 g of methyl iodide in 5 ml of dimethylformamide is added and stirring is continued for 20 hours at room temperature. The reaction mixture is filtered, poured into water, and is extracted with ether.

Workup

  1. additionAfter the addition
  2. additionis added
  3. filtrationThe reaction mixture is filtered
  4. additionpoured into water
  5. extractionthe mixture is extracted with ether
  6. customRemoval of the solvent and trituration with isopropyl ether
  7. customgives an oil
  8. stirringstirring
  9. waitis continued for 20 hours at room temperature
  10. filtrationThe reaction mixture is filtered
  11. additionpoured into water
  12. extractionis extracted with ether

Sources & evidence

ORD record
ord-0c505af5063e4be6997023e6ddca8897
Source dataset
uspto-grants-1985_07
Patent number
US04526982

Reaction notes

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