p-Toluenesulfonic acid → HCID 56942859, compound

HRID 1045390Notes

Reaction equation

HRID 1045390 reaction equation
[O:1]=[S:2]1(=[O:27])[C:8]2[CH:9]=[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:24]=[CH:25][CH:26]=3)[C:17]([NH:19]/[C:20](=[N:22]\[OH:23])/[CH3:21])=O)[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][NH:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:21][C:20]1[N:19]=[C:17]([C:16]2[CH:15]=[C:14]([CH:26]=[CH:25][CH:24]=2)[O:13][C:10]2[CH:11]=[CH:12][C:7]3[O:6][CH2:5][CH2:4][NH:3][S:2](=[O:27])(=[O:1])[C:8]=3[CH:9]=2)[O:23][N:22]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 136381317HCID 136381317, compound

Product 1

HCID 56942859HCID 56942859, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 390 mg (0.99 mmol) of the product obtained in Step B above in 50 ml of toluene there are added 35 mg of para-toluenesulphonic acid and the reaction mixture is heated at reflux using a Dean-Stark system for 12 hours. After evaporation, the crude reaction product is purified over silica gel eluting with a mixture of CH2Cl2/AcOEt 9/1 to yield the expected product.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux
  3. customfor 12 hours
  4. customAfter evaporation
  5. customthe crude reaction product
  6. customis purified over silica gel eluting with a mixture of CH2Cl2/AcOEt 9/1

Sources & evidence

ORD record
ord-2d2241303a87454c84351d679505164a
Source dataset
uspto-grants-2013_10
Patent number
US08569285B2

Reaction notes

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