Pivaloyl chloride → N-(3-Nitro-2,4-dimethyl-benzyl)-2,2-dimethyl-propionamide

HRID 410081Notes

Reaction equation

HRID 410081 reaction equation
[N+:1]([C:4]1[C:5]([CH3:13])=[C:6]([CH:9]=[CH:10][C:11]=1[CH3:12])[CH2:7][NH2:8])([O-:3])=[O:2].[CH3:14][C:15]([CH3:20])([CH3:19])[C:16](Cl)=[O:17]>C1COCC1>[N+:1]([C:4]1[C:5]([CH3:13])=[C:6]([CH:9]=[CH:10][C:11]=1[CH3:12])[CH2:7][NH:8][C:16](=[O:17])[C:15]([CH3:20])([CH3:19])[CH3:14])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 568399723-Nitro-2,4-dimethyl-benzylamine

Product 1

HCID 68032644N-(3-Nitro-2,4-dimethyl-benzyl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Nitro-2,4-dimethyl-benzylamine (1.40 g, crude) is added to a mixture of 2,2-dimethyl-propionic acid chloride (0.682 mL, 5.5 mmol) and TEA (1.92 mL, 13.8 mmol) in THF (30 mL) and it is stirred overnight. The reaction mixture is concentrated, diluted with EtOAc, washed successively with 2 M aq. HCl-solution, 5% aq. NaHCO3 solution and water, dried with Na2SO4 filtered and concentrated.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with EtOAc
  3. washwashed successively with 2 M aq. HCl-solution, 5% aq. NaHCO3 solution and water
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aef7c22ab4a34b67a745f5575bb9f39d
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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