Sulfuric Acid → HCID 21547113, compound

HRID 1605645Notes

Reaction equation

HRID 1605645 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:19])[CH2:15][C:16](N)=[O:17])=[CH:10][CH:9]=1.[CH3:20][Mg]I.[Mg].CI.S(=O)(=O)(O)O>C(Cl)Cl.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:19])[CH2:15][C:16](=[O:17])[CH3:20])=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 21547095HCID 21547095, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 21547113HCID 21547113, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 25.7 gm (0.1 mol) of 3-(2'-fluoro-4-biphenylyl)-butyramide in 750 ml of dry methylene chloride was added dropwise over a period of one hour to a methyl magnesium iodide solution which was prepared from 12.2 gm (0.5 mol) of magnesium and 71 gm (0.5 mol) of methyl iodide in a total of 400 ml of anhydrous ether, and the resulting mixture was refluxed for 6 hours to make the reaction go to completion. After cooling, the reaction mixture was stirred into a mixture consisting of 2 kg of ice and 100 ml of concentrated sulfuric acid. The ethereal phase was separated, washed twice with water, once with an aqueous saturated sodium bicarbonate solution, and again with water, dried over anhydrous magnesium sulfate and evaporated in vacuo. The solid residue was recrystallized twice from gasoline (b.p. range 60° to 80°C), yielding 22.0 gm (86% of theory) of the colorless crystalline compound, m.p. 60°-61°C, of the formula ##SPC22##

Workup

  1. temperaturethe resulting mixture was refluxed for 6 hours
  2. temperatureAfter cooling
  3. customThe ethereal phase was separated
  4. washwashed twice with water, once with an aqueous saturated sodium bicarbonate solution
  5. dry with materialagain with water, dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe solid residue was recrystallized twice from gasoline (b.p. range 60° to 80°C)
  8. customyielding 22.0 gm (86% of theory) of the colorless crystalline compound, m.p. 60°-61°C

Sources & evidence

ORD record
ord-51d5172ea1df485e95806424036396d3
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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