Iodoform → (E)-N-(4-chlorophenyl)-4-iodo-2,2-dimethyl-3-butenamide

HRID 2166312Notes

Reaction equation

HRID 2166312 reaction equation
[CH:1]([I:4])(I)I.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:19])[C:14]([CH3:18])([CH3:17])[CH:15]=O)=[CH:8][CH:7]=1>C1COCC1.[Cr](Cl)(Cl)=O>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:19])[C:14]([CH3:17])([CH3:15])/[CH:18]=[CH:1]/[I:4])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 6374IodoformHCID 15085728N-(4-chlorophenyl)-2,2-dimethyl-3-oxopropanamide

Product 1

HCID 15085692(E)-N-(4-chlorophenyl)-4-iodo-2,2-dimethyl-3-butenamideYield 35.5%

Reagents, catalysts & solvents 2

HCID 178526110HCID 178526110, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of chromous chloride (3.3 g) in 75 mL of dry THF was added a solution of iodoform (3.5 g) and N-(4-chlorophenyl)-2,2-dimethyl-3-oxopropanamide (1 g) in 25 mL of THF, dropwise over 10 minutes. The solution was allowed to stir an additional 1.5 hour, then poured into 100 g of ice water and extracted into ether. The organic phase was dried, filtered and evaporated, and the residue was filtered through a small silica gel column, eluting with ether, to remove chromium residues. The title product (0.55 g) was isolated as a solid, m.p. 145°-146° C.

Workup

  1. extractionextracted into ether
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. filtrationthe residue was filtered through a small silica gel column
  6. washeluting with ether
  7. customto remove chromium residues

Sources & evidence

ORD record
ord-115c246a1f6e438d8907de34a6b89577
Source dataset
uspto-grants-1990_07
Patent number
US04944795

Reaction notes

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