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

HRID 508871노트

반응식

HRID 508871 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3412131dc5574650a0e910aa653bea1c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096545B2

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