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

HRID 2042786Notes

Reaction equation

HRID 2042786 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-a6e5ba0dd04c4ab4af39ebc12a93261a
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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