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

HRID 508871ノート

反応式

HRID 508871 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 dilute 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 dilute 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-3412131dc5574650a0e910aa653bea1c
出典データセット
uspto-grants-2015_08
特許番号
US09096545B2

反応ノート

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