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

HRID 1616059

反応式

HRID 1616059 の反応式
C(N(CC)C(C)C)(C)C.Cl.[CH3:11][NH:12][O: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:12]([O:13][CH3:14])[CH3:11])=[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 N,N-diisopropylethylamine (13.47 mL, 77 mmol) and N,O-dimethylhydroxylamine hydrochloride (7.55 g, 77 mmol) in CHCl3 (117 mL) was added 2-amino-5-fluorobenzoic acid (10.00 g, 64.5 mmol) followed by EDC (12.36 g, 64.5 mmol). The reaction was stirred from 0° C. to rt. After 22 h, the mixture was diluted with DCM (100 mL) and washed with aq satd NaHCO3 (1×100 mL), brine (1×100 mL), and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a brown syrup. The crude material was purified by silica gel column chromatography eluting with a gradient of 0% to 100% EtOAc in hexane, to provide 2-amino-5-fluoro-N-methoxy-N-methylbenzamide as a yellow oil: 1H NMR (400 MHz, DMSO-d6) δ ppm 6.97-7.04 (2H, m), 6.72 (1H, dd, J=9.4, 4.9 Hz), 5.22 (2H, s), 3.54 (3H, s), 3.22 (3H, s); LC-MS (ESI) m/z 199.0 [M+H]+.

後処理

  1. washwashed with aq satd NaHCO3 (1×100 mL), brine (1×100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated in vacuo
  5. customto give the crude material as a brown syrup
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with a gradient of 0% to 100% EtOAc in hexane

出典と根拠

ORDレコード
ord-09d42ad35dc348698994bd7cd6938c88
出典データセット
uspto-grants-2014_07
特許番号
US08765768B2

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