p-Toluenesulfonic acid → HCID 18673896, compound

HRID 1635994Notes

Reaction equation

HRID 1635994 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C:19]3=[O:24])=[CH:12][CH:13]=1)=[O:6].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:40](OC(C)=C)(=[O:42])[CH3:41]>>[C:40]([O:24][C:19]1[C:20]2[C:16](=[C:15]([O:14][C:11]3[N:10]=[CH:9][C:8]([NH:7][C:5](=[O:6])[C:4]4[CH:25]=[CH:26][C:27]([Cl:28])=[C:2]([Cl:1])[CH:3]=4)=[CH:13][CH:12]=3)[CH:23]=[CH:22][CH:21]=2)[CH2:17][CH:18]=1)(=[O:42])[CH3:41]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7916Isopropenyl acetateHCID 9909644HCID 9909644, compound

Product 1

HCID 18673896HCID 18673896, compound

Conditions

Temperature
70 °C

Procedure

A mixture of 1.00 g of 3,4-dichloro-N1-[6-(1-oxo-2,3-dihydro-1H-inden-4-yl)oxy]-3-pyridinyl]benzamide obtained in Example 1, 50 mg of p-toluenesulfonic acid and 5 ml of isopropenyl acetate was stirred overnight at 70° C. The reaction mixture was concentrated and the resulting residue was extracted with ethyl acetate. This extracted solution was washed in turn with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (2:1)) to obtain the titled compound (230 mg, white powder). Melting point: 161-164° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe resulting residue was extracted with ethyl acetate
  3. washThis extracted solution was washed in turn with a saturated sodium hydrogencarbonate solution
  4. dry with materiala saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (2:1))

Sources & evidence

ORD record
ord-b97c40a3dd31400989c5e2f646a662ab
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

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