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

HRID 410067Notes

Reaction equation

HRID 410067 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[N+:8]([C:11]1[C:12]([Cl:20])=[C:13]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:14][NH2:15])([O-:10])=[O:9]>C1COCC1>[N+:8]([C:11]1[C:12]([Cl:20])=[C:13]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:14][NH:15][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 56839971(2,4-Dichloro-3-nitrophenyl)methanamine

Product 1

HCID 67958116N-(3-Nitro-2,4-dichloro-benzyl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2-Dimethyl-propionic acid chloride (0.124 mL, 1.01 mmol) is added to a mixture of 3-nitro-2,4-dichloro-benzylamine (0.28 g, 1.01 mmol) and TEA (0.35 mL, 2.52 mmol) in THF (10 mL) and it is stirred overnight. The reaction mixture is concentrated, diluted with EtOAc, washed successively with 5% aq. NaHCO3 solution and brine, dried with Na2SO4 filtered and concentrated.

Workup

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

Sources & evidence

ORD record
ord-a4fbe7c91ab04e5b981e2cf96a827264
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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