Pivaloyl chloride → N-(2-amino-4-chloro-5-nitrobenzyl)pivalamide

HRID 59379ノート

反応式

HRID 59379 の反応式
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([Cl:12])=[CH:5][C:4]=1[NH2:13].[C:14](Cl)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[NH2:13][C:4]1[CH:5]=[C:6]([Cl:12])[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][NH:1][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]

参加物

4

反応物 2

HCID 62493Pivaloyl chlorideHCID 900190742-(Aminomethyl)-5-chloro-4-nitrobenzenamine

生成物 1

HCID 90018960N-(2-amino-4-chloro-5-nitrobenzyl)pivalamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(aminomethyl)-5-chloro-4-nitrobenzenamine (2.5 g, 12.25 mmol) in THF (35 mL), TEA (3.0 mL) and pivaloyl chloride (1.96 mL, 14.7 mmol) were added and the reaction mass was stirred at RT for 5 h. The reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was washed with dilute HCl and diluted sodium bicarbonate solution, separated, dried over anhydrous sodium sulphate and concentrated to afford 2.0 of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.12 (s, 9H), 4.30 (d, J=5.4 Hz, 2H), 7.81 (d, J=9.9 Hz, 1H), 7.96 (d, J=6.3 Hz, 1H), 8.21 (m, 1H).

後処理

  1. customThe reaction mass was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with dilute HCl and diluted sodium bicarbonate solution
  4. customseparated
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-34d8a4355498420fa0769eef7b44ba5f
出典データセット
uspto-grants-2016_09
特許番号
US09439890B2

反応ノート

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