Iodine → Methyl 4-iodo-3-phenylisothiazole-5-carboxylate

HRID 1948543Notes

Reaction equation

HRID 1948543 reaction equation
N[C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[I:17]I.N(OCCCCC)=O>C(Cl)(Cl)Cl>[I:17][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 807IodineHCID 10026Pentyl nitriteHCID 13073192Methyl 4-amino-3-phenyl-1,2-thiazole-5-carboxylate

Product 1

HCID 58374164Methyl 4-iodo-3-phenylisothiazole-5-carboxylateYield 40.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 4-amino-3-phenylisothiazole-5-carboxylate (500 mg, 2.134 mmol) in chloroform (15 mL) was added iodine (287 mg, 11.31 mmol) and amyl nitrite (0.430 mL, 3.20 mmol). The resulting mixture was heated at reflux for 30 min., cooled to room temperature, washed with aqueous sodium thiosulfate and water. The organic layer was dried over Na2SO4. Removal of the solvent in vacuo and crystallization from ethanol yielded methyl 4-iodo-3-phenylisothiazole-5-carboxylate (300 mg, 0.869 mmol, 40.7% yield) as a pale yellow solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 30 min.
  3. washwashed with aqueous sodium thiosulfate and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customRemoval of the solvent
  6. customin vacuo and crystallization from ethanol

Sources & evidence

ORD record
ord-ca52ce27c9984085a16bfad3726c8157
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

Loading…