Methyl p-toluenesulfonate →

HRID 1241950Notes

Reaction equation

HRID 1241950 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[O:15]2)[S:10][C:9]1=[S:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1([CH3:36])[CH:30]=[CH:29][C:28]([S:31]([O:34]C)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[C:25]1([CH3:36])[CH:26]=[CH:27][C:28]([S:31]([O-:34])(=[O:32])=[O:33])=[CH:29][CH:30]=1.[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[O:15]2)[S:10][CH2+:9]1[S:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 72639901HCID 72639901, compound

Product 0

No Product data yet.

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

To a 10 mL flask was added 3-benzyl-5-(3-methyl-3H-benzoxazol-2-ylidene)-2-thioxothiazolidin-4-one (100 mg, 0.28 mmol), anhydrous CHCl3 (2 mL) and methyl p-toluenesulfonate (53 μL, 0.35 mmol). After heating at reflux 10 min, the reaction mixture was heated at 120° C. for 2 h to yield a red oil. The desired intermediate, 3-benzyl-5-(3-methyl-3H-benzoxazol-2-ylidene)-2-methylthio-4-oxo-2-thiazolium p-toluenesulfonate, was not isolated successfully in previous experiments similar to Example 1 and, thus, the crude reaction mixture was diluted with anhydrous CHCl3 (4 mL) and used without purification in the next step.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux 10 min
  3. customto yield a red oil

Sources & evidence

ORD record
ord-df01522c9dfa4883bd3be5412f3434de
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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