Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(4-chloro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamide

HRID 83857ノート

反応式

HRID 83857 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[CH:4][C:3]=1[O:14][CH3:15].Cl.[CH3:17][NH:18][O:19][CH3:20].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([N:18]([O:19][CH3:20])[CH3:17])=[O:11])=[CH:4][C:3]=1[O:14][CH3:15]

参加物

6

反応物 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667403622-(4-Chloro-3-methoxyphenyl)-2-methylpropanoic acid

生成物 1

HCID 866622432-(4-chloro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamide収率 96%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(4-chloro-3-methoxyphenyl)-2-methylpropanoic acid (15) (268 g, 1.17 mol) in CH2Cl2 (1.7 L) was added N,O-dimethylhydroxylamine hydrochloride (137 g, 1.4 mol), EDCl (270 g, 1.4 mol), and DMAP (172 g, 1.4 mol ). The resulting mixture was stirred for 3 h and washed with 10% citric acid solution (1.5 L), satd NaHCO3 (1.5 L), and brine(1.5 L) successfully. The organic phase was dried over MgSO4, filtered, and concentrated at reduced pressure to afford 2-(4-chloro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamide (16) as a brown solid (276 g, 96%). 1H NMR (400 MHz, CDCl3): δ 7.30-7.32 (d, 1H), 6.81-6.84 (m, 3H), 3.89 (s, 3H), 3.12 (s, 3H), 2.78 (s, 3H), 1.53 (s, 6H).

後処理

  1. washwashed with 10% citric acid solution (1.5 L), satd NaHCO3 (1.5 L), and brine(1.5 L) successfully
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure

出典と根拠

ORDレコード
ord-255fce8739a14fbfa8332581e445d771
出典データセット
uspto-grants-2014_09
特許番号
US08846739B2

反応ノート

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