p-Toluenesulfonic acid → HCID 23336922, compound

HRID 903611Notes

Reaction equation

HRID 903611 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11][S:12]([CH3:15])(=[O:14])=[O:13])[C:8]([CH3:16])=[CH:7][C:6]=1[OH:17])(=O)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][S:12]([O:11][C:9]1[C:8]([CH3:16])=[CH:7][C:6]2[O:17][C:1]([CH3:2])=[N:4][C:5]=2[CH:10]=1)(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 23336917HCID 23336917, compound

Product 1

HCID 23336922HCID 23336922, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.18 g of 2-acetylamino-4-methanesulfonyloxy-5-methylphenol and 0.8 g of p-toluenesulfonic acid were added to 100 ml of toluene and heated at reflux for 12 hours. After cooling and washing with water, concentration under a reduced pressure yielded crude crystals of 5-methanesulfonyloxy-2,6-dimethylbenzoxazole. Immediately the product was dissolved in 50 ml of methanol, to which 5 ml of water containing 2 g of sodium hydroxide was added. A crystalline product was obtained after 1 hour of reflux followed by neutralization with hydrochloric acid after cooling.

Workup

  1. temperatureheated
  2. temperatureat reflux for 12 hours
  3. temperatureAfter cooling
  4. washwashing with water, concentration under a reduced pressure

Sources & evidence

ORD record
ord-e357c347da404f5a8a8186b2adbe89c8
Source dataset
uspto-grants-1980_10
Patent number
US04228233

Reaction notes

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