Iodoxybenzene → HCID 86655984, compound

HRID 1188748Notes

Reaction equation

HRID 1188748 reaction equation
CC1(C)OO1.[I:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].IC1C=CC([C:22]2[S:23][C:24]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:25]=3[N:26]=2)=CC=1>ClCCl>[I:6]([C:9]1[CH:14]=[CH:13][C:12]([C:22]2[S:23][C:24]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:25]=3[N:26]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 101840IodoxybenzeneHCID 115197DimethyldioxiraneHCID 67081740HCID 67081740, compound

Product 1

HCID 86655984HCID 86655984, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A freshly prepared dimethyldioxirane solution (30 mL), as described above (para. [0035]) for the synthesis of simple iodylbenzene analogs, was added drop wise with stirring to an anhydrous dichloromethane (15 mL) solution of 4 (100 mg, 0.28 mmol) cooled in an ice bath. The resultant suspension was stirred at 0° C. for additional period of 2-3 hours and then at room temperature overnight. The yellow solid that was formed was collected by centrifugation and washed three times with dichloromethane. The residue was dried in vacuum to give 2-(4-iodylphenyl)-6-methoxy-1,3-benzothiazole (7) (95.4 mg, 84%) as a beige solid.

Workup

  1. additionwas added drop wise
  2. temperaturecooled in an ice bath
  3. customat room temperature
  4. customovernight
  5. customThe yellow solid that was formed
  6. customwas collected by centrifugation
  7. washwashed three times with dichloromethane
  8. customThe residue was dried in vacuum

Sources & evidence

ORD record
ord-ce54a8482a2046ae913743c35f2ead7a
Source dataset
uspto-grants-2014_03
Patent number
US08674101B2

Reaction notes

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