p-Toluenesulfonic acid → N'-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide

HRID 1673191Notes

Reaction equation

HRID 1673191 reaction equation
[Br:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.COC(OC)OC.[C:18]1([CH3:28])C=CC(S(O)(=O)=O)=CC=1.[CH3:29][NH:30][CH2:31]C>COC(C)(C)C>[Br:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([N:6]=[CH:29][N:30]([CH2:18][CH3:28])[CH3:31])=[C:4]([CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 12219N-MethylethylamineHCID 81671304-Bromo-2,5-dimethylaniline

Product 1

HCID 59843687N'-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamideYield 39%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a mixture of 10.0 g (50 mmol) of 4-bromo-2,5-dimethylaniline and 126 ml (1.15 mol) of trimethoxymethane 0.86 g (5 mmol) of p-toluene sulfonic acid were added. The reaction mixture was refluxed for 16 hrs and concentrated in vacuo. The crude product was solved in 50 ml of dichloro methane and 5.9 g (100 mmol) N-methylethanamine were added. The reaction mixture was stirred for 16 hrs at room temperature. The reaction mixture was concentrated in vacuo. Column chromatographic (gradient: petroleum ether->methyl-tert.butyl ether) yielded 5.2 g (19.5 mmol) 39% of N′-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=1.36.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for 16 hrs
  3. concentrationconcentrated in vacuo
  4. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d0f5f92e86704040b95d049604d91ed4
Source dataset
uspto-grants-2011_08
Patent number
US07999137B2

Reaction notes

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