Methyl iodide → 2-tert-Butyl-6-chloro-7-methanesulfonyl-benzooxazole

HRID 1927569Notes

Reaction equation

HRID 1927569 reaction equation
[O-]S([O-])=O.[Na+].[Na+].[C:7]([O-])(O)=O.[Na+].[C:12]([C:16]1[O:17][C:18]2[C:24]([S:25](Cl)(=[O:27])=[O:26])=[C:23]([Cl:29])[CH:22]=[CH:21][C:19]=2[N:20]=1)([CH3:15])([CH3:14])[CH3:13].IC>O.CCO>[C:12]([C:16]1[O:17][C:18]2[C:24]([S:25]([CH3:7])(=[O:27])=[O:26])=[C:23]([Cl:29])[CH:22]=[CH:21][C:19]=2[N:20]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 234477912-Tert-butyl-6-chlorobenzoxazole-7-sulfonyl chloride

Product 1

HCID 671284462-tert-Butyl-6-chloro-7-methanesulfonyl-benzooxazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 204 mg of Na2SO3 and 409 mg of NaHCO3 in 4 ml H2O is heated to 75° and treated portionwise with 0.5 g of 2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl chloride (US 2007/0249672 page 9). A mixture obtained is heated at 75° for 2 hours and 4 ml of EtOH are added followed by 0.11 ml of iodomethane. A mixture obtained is heated at 90° overnight and allowed to cool to rt. A mixture obtained is extracted with 3×30 ml of EtOAc and the combined organic extracts obtained are washed with brine, dried over MgSO4 and solvent is evaporated. The title compound is obtained.

Workup

  1. customA mixture obtained
  2. temperatureis heated at 75° for 2 hours
  3. customA mixture obtained
  4. temperatureis heated at 90° overnight
  5. customA mixture obtained
  6. extractionis extracted with 3×30 ml of EtOAc
  7. customthe combined organic extracts obtained
  8. washare washed with brine
  9. dry with materialdried over MgSO4 and solvent
  10. customis evaporated

Sources & evidence

ORD record
ord-0bad674880684087a3612d1633aa744b
Source dataset
uspto-grants-2012_05
Patent number
US08183281B2

Reaction notes

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