Water → HCID 19735140, compound

HRID 326577Notes

Reaction equation

HRID 326577 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[NH:8][C:7](=[O:13])[C:6]=2[CH:14]=1.[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>C(O)CC(C)C.[Cu]>[CH3:11][C:9]1([CH3:12])[NH:8][C:7](=[O:13])[C:6]2[CH:14]=[C:2]([S:21][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:3]=[CH:4][C:5]=2[O:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 10494625HCID 10494625, compound

Product 1

HCID 19735140HCID 19735140, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 31260Isoamyl AlcoholSolvent

Procedure

6-Iodo-2,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one (compound A-11, 10.0 g), thiophenol (17.2 g), potassium carbonate (10.0 g) and copper powder (1.0 g) were suspended in isoamyl alcohol (100 ml) and the suspension was heated to reflux for 3 hours under Ar. After air cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was successively washed with an aqueous sodium bicarbonate solution and saturated saline solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (2:1) to obtain 2,2- dimethyl-6-phenylthio-3,4-dihydro-2H-1,3-benzoxazin-4-one (2.67 g) (Compound A-12). The physical properties are shown in Table 1.

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 3 hours under Ar
  3. temperatureAfter air cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was successively washed with an aqueous sodium bicarbonate solution and saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (2:1)

Sources & evidence

ORD record
ord-f8a73343820c4b4fa0a12d656a6cf3a8
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

Loading…