Methanesulfonyl chloride → N-(5-Acetyl-2-chlorophenyl)methanesulfonamide

HRID 1794714노트

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HRID 1794714 반응식
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:17])=[C:8]([NH:10]C2C=CC=CC=2)[CH:9]=1)(=[O:3])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.N1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:17])=[C:8]([NH:10][S:19]([CH3:18])(=[O:21])=[O:20])[CH:9]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 69654843HCID 69654843, 화합물

생성물 1

HCID 22220251N-(5-Acetyl-2-chlorophenyl)methanesulfonamide수율 57%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a stirred solution of 5-acetyl-2-chloro-phenylaniline (which was obtained in Example 22) (7.40 g, 43.5 mmol) in CH2Cl2 (200 mL) and pyridine (40 mL) at 0˜5° C. was added dropwise methanesulfonyl chloride (5.0 g, 43.6 mmol) in 50 mL of CH2Cl2. After 1 hour at 0° C. the mixture was warmed to room temperature and stirred at room temperature for another hour. The solvents were removed and the residue was dissolved in CH2Cl2 (500 mL). The reaction mixture was washed with water and the organic layer was dried (MgSO4) and concentrated. The product was purified by flash silica gel chromatography eluting with ethyl acetate and hexanes to give the title compound as a white solid (6.1 g, 57%); 1H NMR (300 MHz, DMSO-d6) δ 2.58(s, 3 H), 3.08(s, 3 H), 7.69(d, J=8.3 Hz, 1 H), 7.83(dd, J=8.3, 2.1 Hz, 1 H), 7.94(d, J=2.1 Hz, 1 H), 9.69(s, 1 H); MS (ES) m/z: 245.9 ((M−H)−, 100%); HRMS Calcd. for C9H11ClNO3S(MH+): 248.0148. Found: 248.0135.

후처리

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in CH2Cl2 (500 mL)
  3. washThe reaction mixture was washed with water
  4. dry with materialthe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe product was purified by flash silica gel chromatography
  7. washeluting with ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-df6cd6ed48e24aeaab242c504d2864c3
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022716B2

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