Iodoethane → HCID 12879399, compound

HRID 225100Notes

Reaction equation

HRID 225100 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 145 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-b119a69968dd4eb3821106b2ac164e71
Source dataset
uspto-grants-1980_11
Patent number
US04235619

Reaction notes

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