Dimethylformamide → HCID 21938647, compound

HRID 1596645Notes

Reaction equation

HRID 1596645 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([I:13])=[C:7]([CH2:9][C:10](O)=[O:11])[CH:8]=1)[CH3:2].CN(C=O)C.S(Cl)([Cl:21])=O>C(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([I:13])=[C:7]([CH2:9][C:10]([Cl:21])=[O:11])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 21938638HCID 21938638, compound

Product 1

HCID 21938647HCID 21938647, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Ethyl-2-iodophenylacetic acid is dissolved in methylene chloride (400 ml) and DMF (1 ml) is added. Thionyl chloride (21 ml, 300 mmol) is then added dropwise over 20 minutes. The mixture is heated to reflux and heating continued for 3.5 hours when the mixture is cooled and ice-water (400 ml) and methylene chloride (300 ml) are added. The layers are separated, the organic layer is washed with a sodium bicarbonate solution, saturated brine, dried (magnesium sulfate), and evaporated under reduced pressure to yield 5-ethyl-2-iodophenylacetyl chloride.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperatureheating
  4. temperaturewhen the mixture is cooled
  5. customThe layers are separated
  6. washthe organic layer is washed with a sodium bicarbonate solution, saturated brine
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1039987b16fe4afda7fccdb0399b3843
Source dataset
uspto-grants-2001_09
Patent number
US06291523B1

Reaction notes

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