Dichloromethane → 5-bromo-4-chloro-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-benzenesulfonamide

HRID 2382679노트

반응식

HRID 2382679 반응식
C(Cl)Cl.[Br:4][C:5]1[C:6]([Cl:16])=[CH:7][C:8]([F:15])=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:10]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][CH3:26].C(N(CC)CC)C>O>[Br:4][C:5]1[C:6]([Cl:16])=[CH:7][C:8]([F:15])=[C:9]([S:11]([N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[O:18][CH3:17])[CH3:26])(=[O:13])=[O:12])[CH:10]=1

참가 물질

6

반응물 4

HCID 6344Dichloromethane2회HCID 8471TriethylamineHCID 27595792-Methoxy-N-methylanilineHCID 566047345-Bromo-4-chloro-2-fluoro-benzenesulfonyl chloride

생성물 1

HCID 684711855-bromo-4-chloro-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-benzenesulfonamide수율 61.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of DCM (36 mL) containing 5-bromo-4-chloro-2-fluoro-benzenesulfonyl chloride (5.5 g, 17.9 mmol) was added (2-methoxy-phenyl)-methyl-amine (2.6 g, 18.8 mmol) and triethylamine (7.1 mL, 53.7 mmol). The mixture was stirred for 16 hrs. 100 mL of DCM and 100 mL of water were added. The organic layer was separated, washed with water (2×50 mL) and dried over MgSO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (9/1 to 5/1) yielded 5-bromo-4-chloro-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-benzenesulfonamide as a white solid (4.5 g). MS: 408.0 (M+H)+; tR=8.83 min (method 2). NMR (CDCl3), δ, 7.925 (1H, d, J=6.9 Hz), 7.257-7.367 (3H, m), 6.959 (1H, m), 6.831 (1H, d, m), 3.490 (3H, s), 3.339 (3H, d, J=2.4 Hz).

후처리

  1. customThe organic layer was separated
  2. washwashed with water (2×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationConcentration and purification by silica gel column chromatography
  5. washeluting with hexane/ethyl acetate (9/1 to 5/1)

출처 및 근거

ORD 기록
ord-d2c046555c054bc38f3d5439ebf7fb34
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263588B2

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