Ammonium Hydroxide → 2-Methoxy-4-nitrobenzenesulfonamide

HRID 383736

반응식

HRID 383736 반응식
[OH-].[NH4+:2].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[S:14](Cl)(=[O:16])=[O:15]>[NH4+].[Cl-]>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[S:14]([NH2:2])(=[O:16])=[O:15]

참가 물질

4

반응물 2

HCID 14923Ammonium HydroxideHCID 3094582-Methoxy-4-nitrobenzenesulfonyl chloride

생성물 1

HCID 203309102-Methoxy-4-nitrobenzenesulfonamide수율 68.9%

시약·촉매·용매 1

HCID 25517Ammonium Chloride용매

실험 절차

To a concentrated solution of ammonium hydroxide (28%, 2.5 mL, 20 mmol) was added cautiously 2-methoxy-4-nitrobenzenesulfonyl chloride (0.25 g, 1.0 mmol). After stirring 24 h the reaction mixture was added to satd NH4Cl (50 mL) and extracted with DCM (2×50 mL). The combined extracts were washed with brine, dried (anhyd Na2SO4) and concentrated under reduced pressure. The crude residue was chromatographed (silica, MeOH/DCM, 0:100 to 10:90) to yield 2-methoxy-4-nitrobenzenesulfonamide (0.16 g, 68%) as a pale brown solid. 1H-NMR (DMSO-d6) δ 7.99 (1H, d), 7.90-7.95 (2H, m), 7.47 (2H, br s), 4.04 (3H, s). The title compound was prepared from 2-methoxy-4-nitrobenzenesulfonamide in a manner similar to that described for Example 3A. 1H-NMR (DMSO-d6) δ 9.69 (1H, s), 8.01 (1H, d, J=8.1), 7.92 (1H, app t, J=7.6), 7.81 (1H, app t, J=7.6), 7.74 (1H, d, J=1.8), 7.63 (1H, d, J=8.6), 7.50 (1H, d, J=7.6), 7.47 (1H, dd, J=1.8, 8.6), 6.93 (2H, s), 6.66 (1H, s), 3.88 (3H, s), 2.14 (3H, s), 1.89 (3H, s); MS (ESI): 468 (MH+). B. In a similar manner as that described for Example 6A, the following was prepared by replacing ammonium hydroxide with dimethylamine:

후처리

  1. extractionextracted with DCM (2×50 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (anhyd Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was chromatographed (silica, MeOH/DCM, 0:100 to 10:90)

출처 및 근거

ORD 기록
ord-9ee92997634247f5b7182aee7363f65f
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367667B2

연결된 노트

불러오는 중…