Pivaloyl chloride → N-(3-Amino-2,4-dichlorobenzyl)pivalamide

HRID 1189609Notes

Reaction equation

HRID 1189609 reaction equation
[NH2:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH2:6].[CH3:12][C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15]>C1COCC1>[NH2:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH:6][C:14](=[O:15])[C:13]([CH3:18])([CH3:17])[CH3:12]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 568399683-(Aminomethyl)-2,6-dichloroaniline

Product 1

HCID 56839975N-(3-Amino-2,4-dichlorobenzyl)pivalamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-2,4-dichloro-benzylamine (2.28 g, 11.9 mmol) is added to a mixture of 2,2-dimethyl-propionic acid chloride (1.47 mL, 11.9 mmol) and TEA (4.14 mL, 29.8 mmol) in THF (90 mL) and it is stirred for 3 h. The reaction mixture is concentrated, diluted with EtOAc, washed with 5% aq NaHCO3 solution and water, dried with Na2SO4, filtered and concentrated to give the sub-title compound.

Workup

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

Sources & evidence

ORD record
ord-37a7dd38832e47139d75c9baf199b032
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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