1,2-Dichloroethane → 2-Amino-5-fluoro-N-methoxy-N-methylbenzamide

HRID 19675

반응식

HRID 19675 반응식
C(N(C(C)C)CC)(C)C.Cl.[CH3:11][O:12][NH:13][CH3:14].[NH2:15][C:16]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:17]=1[C:18](O)=[O:19].C(Cl)CCl>C(Cl)(Cl)Cl.C(Cl)Cl>[NH2:15][C:16]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:17]=1[C:18]([N:13]([O:12][CH3:11])[CH3:14])=[O:19]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 1014122-Amino-5-fluorobenzoic acid

생성물 1

HCID 534075722-Amino-5-fluoro-N-methoxy-N-methylbenzamide

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

To a 0° C. mixture of diisopropylethylamine (34.36 mL, 197.25 mmol) and O,N-dimethyl-hydroxylamine hydrochloride (19.24 g, 197.25 mmol) in CHCl3 (300 mL) was added 2-amino-5-fluorobenzoic acid (25.50 g, 164.38 mmol) followed by EDC (31.51 g, 164.38 mmol). The reaction was stirred from 0° C. to ambient temperature over 2 h and then diluted with CH2Cl2 (100 mL), washed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification by normal phase chromatography (3-8% MeOH/CH2Cl2) yielded 2-amino-5-fluoro-N-methoxy-N-methylbenzamide as a yellow oil. 1H NMR (CDCl3, 400 MHz) 7.12 (m, 1H, ArH); 6.93 (m, 1H, ArH); 6.65 (m, 1H, ArH); 3.63 (s, 3H, CH3); 3.35 (s, 3H, CH3); MS (Electrospray): m/z 199.1 (M+H).

후처리

  1. washwashed with saturated sodium bicarbonate solution (100 mL) and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by normal phase chromatography (3-8% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-3d66f49508da4beb9babdb20a9d84317
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745452B2

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