4-Iodobenzoyl chloride → Ethyl 5-(4-iodophenyl)oxazole-4-carboxylate

HRID 2278381Notes

Reaction equation

HRID 2278381 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[N+:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[C-:12]>C1COCC1>[CH2:17]([O:16][C:14]([C:13]1[N:11]=[CH:12][O:7][C:6]=1[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=1)=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 743734-Iodobenzoyl chlorideHCID 533707Ethyl isocyanoacetate

Product 1

HCID 61636738Ethyl 5-(4-iodophenyl)oxazole-4-carboxylateYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-iodobenzoyl chloride (14.0 g, 0.052 mol) in 100 ml THF was added TEA (15.6 g, 0.156 mol) in a dropwise manner and the mixture was stirred for 10 minutes before slowly adding ethyl 2-isocyanoacetate (6.5 g, 0.058 mol). The reaction mixture was stirred at room temperature for 16 hours, the solvent was removed and the residue was treated with EtOAc and water. The organic layer was separated, dried over Na2SO4 and the solvent was removed. The crude product was purified by column to give the title compound (11.0 g, 61.7%) as an orange solid.

Workup

  1. customthe solvent was removed
  2. additionthe residue was treated with EtOAc and water
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed
  6. customThe crude product was purified by column

Sources & evidence

ORD record
ord-b0b8c2fdaa3e4649b3db3a3d26dd0229
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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