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

HRID 508871Notes

Reaction equation

HRID 508871 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3412131dc5574650a0e910aa653bea1c
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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