19524-06-2 → 7-benzenesulfonyl-2,2-dimethyl-4-pyridin-4-yl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 2224086Notes

Reaction equation

HRID 2224086 reaction equation
[C:1]1([S:7]([C:10]2[CH:21]=[CH:20][C:13]3[NH:14][CH2:15][C:16]([CH3:19])([CH3:18])[O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].Br[C:24]1[CH:29]=[CH:28][NH+:27]=[CH:26][CH:25]=1>ClCCl>[C:1]1([S:7]([C:10]2[CH:21]=[CH:20][C:13]3[N:14]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[CH2:15][C:16]([CH3:18])([CH3:19])[O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1127558919524-06-2HCID 586415397-benzenesulfonyl-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine

Product 1

HCID 586415657-benzenesulfonyl-2,2-dimethyl-4-pyridin-4-yl-3,4-dihydro-2H-benzo[1,4]oxazineYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 7-benzenesulfonyl-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine (0.257 g., 0.847 mmol) and 4-bromopyridinium chloride (0.658 g., 3.388 mmol) was heated without solvent at 185° C. for 45 minutes. The reaction mixture was cooled to room temperature, suspended in 5 mL dichloromethane and concentrated in vacuo. The resulting crude oil was dissolved in a mixture of 50 mL ethyl acetate and 50 mL water. The aqueous layer was made strongly basic with 50 mL of 2N aqueous potassium carbonate, and the phases were separated. The organic phase was washed with twice with 50 mL water and once with 50 mL brine, dried over sodium sulfate and concentrated in vacuo. The resulting crude oil was purified by flash chromatography (3% methanol in dichloromethane) to give 161 mg (54%) of 7-benzenesulfonyl-2,2-dimethyl-4-pyridin-4-yl-3,4-dihydro-2H-benzo[1,4]oxazine as a foam. MS: 381 (M+H)+, mp: 112.7-120.4° C. (as hydrochloride salt).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting crude oil was dissolved in a mixture of 50 mL ethyl acetate and 50 mL water
  4. customthe phases were separated
  5. washThe organic phase was washed with twice with 50 mL water
  6. dry with materialonce with 50 mL brine, dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude oil was purified by flash chromatography (3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c43d7ba684374f9cbabd3a0912a8b608
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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