Pyridine → N-(2,2-Dimethoxyethyl)-N-[(2-fluorophenyl)methyl]-4-methylbenzenesulfonamide

HRID 1521568노트

반응식

HRID 1521568 반응식
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][CH2:6][CH:7]([O:10][CH3:11])[O:8][CH3:9].N1C=CC=CC=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[CH3:11][O:10][CH:7]([O:8][CH3:9])[CH2:6][N:5]([CH2:4][C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[F:1])[S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)(=[O:30])=[O:29]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 60657374HCID 60657374, 화합물

생성물 1

HCID 89155471N-(2,2-Dimethoxyethyl)-N-[(2-fluorophenyl)methyl]-4-methylbenzenesulfonamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

N-(2-fluorobenzyl)-2,2-dimethoxyethanamine (BB; 33.0 g, 0.154 mol) were dissolved in 200 mL of dichloromethane and pyridine (50.2 g, 0.417 mol) was added. At 0° C. a solution of p-toluene sulphonyl chloride (58.0 g, 0.201 mol) in dichloromethane (500 mL) was added drop wise. The reaction was allowed to warm to room temperature and stirring is continued until conversion was completed. For workup, the reaction mixture was extracted twice with 2M aqueous hydrochloric acid, twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulphate, evaporated to dryness and the obtained crude product was purified by silica gel chromatography to yield the title compound. 1H NMR (400 MHz, CDCl3) δ 7.69-7.67 (2H, m), 7.43-7.39 (m, 1H), 7.29-7.21 (m, 3H), 7.12-7.08 (m, 1H), 6.99-6.95 (m, 1H), 4.52 (s, 2H), 4.39-4.37 (t, 1H, J=5.2 Hz), 3.26-3.24 (m, 8H), 2.42 (s, 3H).

후처리

  1. extractionFor workup, the reaction mixture was extracted twice with 2M aqueous hydrochloric acid, twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated to dryness
  4. customthe obtained crude product
  5. customwas purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-fe5255bcd2224020906ef728ccd3b9af
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

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