p-Toluenesulfonic acid → HCID 59823518, compound

HRID 1426867Notes

Reaction equation

HRID 1426867 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([O:8][C:9]2[C:15]([CH3:16])=[CH:14][C:12]([NH2:13])=[C:11]([CH3:17])[CH:10]=2)[S:5][C:6]=1[Cl:7].COC(OC)OC.[C:25]1([CH3:35])C=CC(S(O)(=O)=O)=CC=1.[CH3:36][NH:37][CH2:38]C>COC(C)(C)C>[Cl:1][C:2]1[N:3]=[C:4]([O:8][C:9]2[C:15]([CH3:16])=[CH:14][C:12]([N:13]=[CH:36][N:37]([CH2:25][CH3:35])[CH3:38])=[C:11]([CH3:17])[CH:10]=2)[S:5][C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 12219N-MethylethylamineHCID 59823517HCID 59823517, compound

Product 1

HCID 59823518HCID 59823518, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 2.0 g (6.9 mmol) of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline and 11.3 ml (0.13 mol) of trimethoxymethane 0.12 g (0.7 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 12 ml of toluene and 0.82 g (13.8 mmol) N-methylethanamine were added. The reaction mixture was stirred for 16 hrs at 50° C. The reaction mixture was concentrated in vacuo. Column chromatographie (gradient: petroleum ether->methyl-tert. butyl ether) yielded 2.3 g (6.3 mmol) 91% of N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=2.04

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-366a21f447464731b36f6d738c63105a
Source dataset
uspto-grants-2015_01
Patent number
US08933107B2

Reaction notes

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