p-Toluenesulfonic acid → HCID 57814406, compound

HRID 2265119Notes

Reaction equation

HRID 2265119 reaction equation
[I:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.C(OC(O[CH2:19][CH3:20])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:32][NH:33][CH2:34]C>C1CCCCC1.C(OCC)(=O)C>[I:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([N:6]=[CH:32][N:33]([CH2:19][CH3:20])[CH3:34])=[C:4]([CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 12219N-MethylethylamineHCID 31214Ethyl orthoformateHCID 4770984(4-Iodo-2,5-Dimethylphenyl)Amine

Product 1

HCID 57814406HCID 57814406, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 12.3 g (50 mmol) of 4-iodo-2,5-dimethylaniline and 83 ml (500 mmol) of triethoxymethane 0.48 g (2.50 mmol) of p-toluene sulfonic acid were added. The reaction mixture was refluxed for 16 hrs and concentrated in vacuo. The crude product was dissolved in 100 ml of dichloromethane and 5.91 g (100 mmol) N-methylethanamine were added. The reaction mixture was stirred for 16 hrs at 40° C. The reaction mixture was concentrated in vacuo. Column chromatographie (cyclohexane/ethyl acetate 3:1) yielded 13.4 g (42.3 mmol) 85% of N′-(4-iodo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=1.21.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for 16 hrs
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude product was dissolved in 100 ml of dichloromethane
  5. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a8c22c256337432a9f900a019491277f
Source dataset
uspto-grants-2010_12
Patent number
US07855309B2

Reaction notes

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