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

HRID 1506511Notes

Reaction equation

HRID 1506511 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 58.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 4-amino-3-phenylisothiazole-5-carboxylate (Preparation 103C, 700 mg, 2.99 mmol) in chloroform (80 mL) were added iodine (4019 mg, 15.84 mmol) and amyl nitrite (0.602 mL, 4.48 mmol). The resulting mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and washed with aqueous sodium thiosulfate and then water. The organic layer was dried over sodium sulfate. Removal of the solvent in vacuo and crystallization from ethanol yielded methyl 4-iodo-3-phenylisothiazole-5-carboxylate (600 mg, 1.738 mmol, 58.2% yield) as a pale yellow solid. The compound had an LC/MS M+1=346.0.

Workup

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

Sources & evidence

ORD record
ord-6897a65a9f234ecab98806947d1450d7
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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