Pyridine → Benzenesulfonamide, 4-chloro-3-nitro-N-phenyl-

HRID 230534

반응식

HRID 230534 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].N[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 6115AnilineHCID 73244-Chloro-3-nitrobenzenesulfonamide

생성물 1

HCID 67302Benzenesulfonamide, 4-chloro-3-nitro-N-phenyl-수율 96.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Two portions of 4-Chloro-3-nitrobenzenesulfonamide (1.73 g, 6.78 mmol) were dissolved in CH2Cl2 (7.0 mL) in reaction flasks. Aniline (757 mg, 8.13 mmol) was added drop-wise at room temperature, followed by slow additions of pyridine (2.0 mL). After 16 h of continued stirring, the reaction mixtures were diluted with ethyl acetate (50 mL) and washed with 1 M HCl (3×50 mL). The organic phases were dried (MgSO4) and evaporated to brown solids, which upon re-crystallization from ethanol/water gave off-white solid of the product 2.04 g (96%): 1H NMR (CDCl3, 400 MHz) δ 8.24 (d, 1H), 7.80 (dd, 1H), 7.61 (d, 1H), 7.30 (t, 2H), 7.20 (t, 1H), 7.09 (d, 2H), 6.79 (bs, 1H); MS (CI) 310.8 (M−H)−; Purity (HPLC, Hichrom 200×4.6 mm I.D.)>98%.

후처리

  1. customthe reaction mixtures
  2. washwashed with 1 M HCl (3×50 mL)
  3. dry with materialThe organic phases were dried (MgSO4)
  4. customevaporated to brown solids, which upon re-crystallization from ethanol/water

출처 및 근거

ORD 기록
ord-cde683c2f4e44cf895a311a14fbafc0e
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566715B2

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