Iodine → HCID 67169575, compound

HRID 1506515Notes

Reaction equation

HRID 1506515 reaction equation
[C:1]1([C:7]2[S:11][N:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:16]I.[N+]([O-])(O)=O>CCOC(C)=O>[I:16][C:8]1[C:9]([C:12]([O:14][CH3:15])=[O:13])=[N:10][S:11][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 807IodineHCID 944Nitric AcidHCID 67472041HCID 67472041, compound

Product 1

HCID 67169575HCID 67169575, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To methyl 5-phenylisothiazole-3-carboxylate (500 mg, 2.280 mmol) in a tube were added iodine (579 mg, 2.280 mmol) and nitric acid (2.280 mmol). The resulting mixture was heated to 80° C. for 1 h. After the reaction was cooled to room temperature, EtOAc (50 mL) was added. The resulting mixture was washed with saturated Na2S2O3 solution until the brown color disappeared. The organic layer was concentrated. HPLC and flash chromatography yielded methyl 4-iodo-5-phenylisothiazole-3-carboxylate (168 mg, 0.487 mmol, 21.34% yield). The compound had an LC/MS M+1=345.9.

Workup

  1. temperatureAfter the reaction was cooled to room temperature
  2. washThe resulting mixture was washed with saturated Na2S2O3 solution until the brown color
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-7158e76fefc94397ab92cddacfb0a844
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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