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

HRID 1891358ノート

反応式

HRID 1891358 の反応式
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

参加物

6

反応物 4

HCID 6344Dichloromethane2 回HCID 8471TriethylamineHCID 27595792-Methoxy-N-methylanilineHCID 566047345-Bromo-4-chloro-2-fluoro-benzenesulfonyl chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-68a8ebfb0e2e4e339337ba81df5f5a8a
出典データセット
uspto-grants-2013_08
特許番号
US08507536B2

反応ノート

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