1,2-Dichloroethane → 2-(4-Bromophenyl)-N-isobutyl-2-methylpropanamide

HRID 1175565Notes

Reaction equation

HRID 1175565 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=O)=[CH:4][CH:3]=1.[OH-].[Na+].Cl.BrC1C=CC(C(C)(C)C(O)=O)=CC=1.[CH3:31][CH:32]([CH3:35])[CH2:33][NH2:34].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([NH:34][CH2:33][CH:32]([CH3:35])[CH3:31])=[O:11])=[CH:6][CH:7]=1

Participants

9

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 6558IsobutylamineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 3651431Methyl 2-(4-bromophenyl)-2-methylpropanoateHCID 109336792-(4-Bromophenyl)-2-methylpropanoic acid

Product 1

HCID 687750752-(4-Bromophenyl)-N-isobutyl-2-methylpropanamideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-(4-bromophenyl)-2-methylpropanoate (1.29 ml, 5 mmol) was added to 30 ml of 1M aq. NaOH and the mixture was stirred at 60° C. overnight. The solution was acidified with 6M aq. HCl (pH 2) and extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4 and concentrated on vacuum. The crude 2-(4-bromophenyl)-2-methylpropanoic acid was coupled without further purification with 2-methylpropan-1-amine (0.5 ml, 5 mmol) in presence of EDC (1.1 g, 5.5 mmol) and HOBt (675 mg, 5 mmol) in 8 ml of DMF at rt overnight. The mixture was dried down on vacuum and extracted with EtOAc and washed with saturated NaHCO3, 10% citric acid and brine. Organic extracts were dried over MgSO4 and concentrated on vacuum to give 2-(4-bromophenyl)-N-isobutyl-2-methylpropanamide as a white solid (1.4 g, 94%). (M+H, 298).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated on vacuum
  6. customThe mixture was dried down on vacuum
  7. extractionextracted with EtOAc
  8. washwashed with saturated NaHCO3, 10% citric acid and brine
  9. dry with materialOrganic extracts were dried over MgSO4
  10. concentrationconcentrated on vacuum

Sources & evidence

ORD record
ord-cf4870b5bb964611ad0eeb37932657d1
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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