Dimethylformamide → HCID 21938647, compound

HRID 1280844Notes

Reaction equation

HRID 1280844 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-a2dd52fbbb924c4bb6193431a31365cf
Source dataset
uspto-grants-2002_09
Patent number
US06451858B2

Reaction notes

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