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

HRID 388282
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HRID 388282 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f4ad23439d2c459086be3f661cdaefb6
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377931B2

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