Iodoethane → HCID 12879399, compound

HRID 261773Notes

Reaction equation

HRID 261773 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][N:10]([CH3:21])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:24](I)[CH3:25]>CS(C)=O>[CH2:24]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][N:10]([CH3:21])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1)[CH3:25]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12879397HCID 12879397, compound

Product 1

HCID 12879399HCID 12879399, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 3.2 g. portion of the product of Example 217 was added to a suspension of 0.86 g. of sodium hydride in 50 ml. of dimethylsulfoxide. The mixture was stirred at room temperature, and 3.5 g. of ethyl iodide was added. The mixture was stirred for two and one-half hours more, and extracted with ethyl acetate. The extract was washed with dilute hydrochloric acid and then with water, and dried. The dried extract was then filtered and concentrated to dryness under vacuum. The product was 2.2 g. of 3-(3-ethoxyphenyl)-1-methyl-5-phenyl-4(1H)-pyridone, m.p. 133°-135° C.

Workup

  1. stirringThe mixture was stirred for two and one-half hours more
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with dilute hydrochloric acid
  4. dry with materialwith water, and dried
  5. extractionThe dried extract
  6. filtrationwas then filtered
  7. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-e28246e9fd6a4b788b535e0956fc3adf
Source dataset
uspto-grants-1979_05
Patent number
US04152136

Reaction notes

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