Water → 8-bromo-4-(4-chloro-benzenesulfonyl)-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 388282Notes

Reaction equation

HRID 388282 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Br:12][C:13]1[C:22]2[O:21][CH2:20][CH2:19][NH:18][C:17]=2[CH:16]=[C:15]([CH3:23])[CH:14]=1.N1C=CC=CC=1.O>ClCCl>[Br:12][C:13]1[C:22]2[O:21][CH2:20][CH2:19][N:18]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[C:17]=2[CH:16]=[C:15]([CH3:23])[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 225572458-Bromo-6-methyl-3,4-dihydro-2h-1,4-benzoxazine

Product 1

HCID 225572608-bromo-4-(4-chloro-benzenesulfonyl)-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazineYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-benzenesulfonyl chloride (560 mg, 2.65 mmol) was added in small portions under nitrogen to an ice-cold solution of 8-bromo-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazine (550 mg, 2.41 mmol) and pyridine (381 mg, 4.82 mmol) in dichloromethane (20 mL). After 12 hours at ambient temperature, water was added. The layers were separated. The organic phase was washed with saturated aqueous solution of sodium bicarbonate (20 mL), dried (Na2SO4) and concentrated to give the title compound as a solid (820 mg, 84%). A sample was recrystallized from ethanol. MS: M+=401. M.p. 143.0-145.1° C.

Workup

  1. customThe layers were separated
  2. washThe organic phase was washed with saturated aqueous solution of sodium bicarbonate (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f4ad23439d2c459086be3f661cdaefb6
Source dataset
uspto-grants-2013_02
Patent number
US08377931B2

Reaction notes

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