p-Toluenesulfonic acid → HCID 60135688, compound

HRID 1426868Notes

Reaction equation

HRID 1426868 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[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>C(OCC)(=O)C.C1CCCCC1>[CH2:18]([N:30]([CH3:31])[CH:29]=[N:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([OH:9])=[CH:6][C:7]=1[CH3:8])[CH3:28]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 12219N-MethylethylamineHCID 765444-Amino-2,5-dimethylphenol

Product 1

HCID 60135688HCID 60135688, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 10.0 g (73 mmol) of 4-amino-2,5-dimethylphenol and 73 ml (0.84 mol) of trimethoxymethane 0.73 g (4.2 mmol) of p-toluene sulfonic acid were added and the mixture was heated to reflux for 2 hours. Then the volatiles were removed in vacuo and the residue was dissolved in 73 ml of toluene and 12.9 g (217 mmol) N-methylethanamine were added. The reaction mixture was heated to 50° C. for 20 hrs and concentrated in vacuo. Column chromatographie (gradient: cyclohexane->ethyl acetate) yielded 9.17 g (44 mmol) 55% of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide; log P (pH 2.3)=0.41.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 hours
  4. customThen the volatiles were removed in vacuo
  5. dissolutionthe residue was dissolved in 73 ml of toluene
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75f6a5544d3b4f79997692e8cae5507c
Source dataset
uspto-grants-2015_01
Patent number
US08933107B2

Reaction notes

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