p-Toluenesulfonic acid → HCID 56837185, compound

HRID 576479Notes

Reaction equation

HRID 576479 reaction equation
[C:1]1([CH3:11])C=CC(S(O)(=O)=O)=CC=1.[F:12][CH:13]([F:31])[O:14][C:15]1[CH:16]=[C:17]([S:21][C:22]2[CH:23]=[C:24]([CH3:30])[C:25](=[CH:27][C:28]=2[CH3:29])[NH2:26])[CH:18]=[CH:19][CH:20]=1.CCCCCC.C(OCC)(=O)C.[CH2:44]([NH:46][CH3:47])C>C(Cl)Cl>[CH2:1]([N:46]([CH3:47])[CH:44]=[N:26][C:25]1[CH:27]=[C:28]([CH3:29])[C:22]([S:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH:13]([F:12])[F:31])[CH:16]=2)=[CH:23][C:24]=1[CH3:30])[CH3:11]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 12219N-MethylethylamineHCID 21226206Ethyl acetate hexaneHCID 66584010HCID 66584010, compound

Product 1

HCID 56837185HCID 56837185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Catalytic p-toluenesulfonic acid is added to a mixture of 25 g of 4-(3-difluoromethoxyphenylthio)-2,5-xylidine (0.085 moles) and 141 ml of triethylorthoformiate (0.85 moles). The temperature is brought to reflux and the mixture is kept under stirring for 3 hours. The reaction trend is controlled with TLC (eluent hexane/ethyl acetate 8:2). When the reaction is completed, the mixture is concentrated at reduced pressure and the raw product obtained dissolved in methylene chloride (234 ml); 14.3 ml of N-ethylmethylamine (0.17 moles) are added dropwise. The mixture is kept under stirring for 3 hours at 40° C. and, after TLC control (eluent hexane/ethyl acetate 8:2), is concentrated at reduced pressure. 20 g of the desired product are obtained.

Workup

  1. temperatureto reflux
  2. concentrationthe mixture is concentrated at reduced pressure
  3. customthe raw product obtained
  4. stirringunder stirring for 3 hours at 40° C.
  5. concentrationafter TLC control (eluent hexane/ethyl acetate 8:2), is concentrated at reduced pressure

Sources & evidence

ORD record
ord-44f556ae67104410be8803eafd873db1
Source dataset
uspto-grants-2015_05
Patent number
US09040457B2

Reaction notes

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