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

HRID 19675

反応式

HRID 19675 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3d66f49508da4beb9babdb20a9d84317
出典データセット
uspto-grants-2010_06
特許番号
US07745452B2

関連ノート

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