Ethyl p-methylbenzenesulfonate → HCID 23042805, compound

HRID 2165512Notes

Reaction equation

HRID 2165512 reaction equation
[I-:1].[CH3:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:6]=2[NH+:7]=1.[C:17]1(C)C=CC(S(OCC)(=O)=O)=C[CH:18]=1.[I-]>CO.C(O)C>[I-:1].[CH2:17]([N+:7]1[C:6]2[CH:8]=[C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:11][C:5]=2[O:4][C:3]=1[CH3:2])[CH3:18]

Participants

6

Reactant 3

HCID 6638Ethyl p-methylbenzenesulfonateHCID 30165Iodide IonHCID 23042801HCID 23042801, compound

Product 1

HCID 23042805HCID 23042805, compoundYield 121.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

Intermediate D (4.52 g) and ethyl p-toluenesulfonate (4.4 g) were combined in a large test tube and heated over a hot air gun with manual stirring for 5 minutes. A brownish melt formed, which solidified to a glass on cooling to room temperature. The glas was dissolved in 50 ml hot methanol, diluted with an 100 ml hot ethanol, and 9.0 g tetrabutylamonnium iodide dissolved in 20 ml ethanol was added. The brown, clear solution was cooled to room temperature and then ice cooled for 4 hours. Filtration of the resulting crystalline product gave 5.92 g of 3-ethyl-2-methyl-5-methylsulfonamidobenzoxazolium iodide (Intermediate E).

Workup

  1. temperatureheated over a hot air gun
  2. customA brownish melt formed
  3. additionwas added
  4. temperatureThe brown, clear solution was cooled to room temperature
  5. temperatureice cooled for 4 hours
  6. filtrationFiltration of the resulting crystalline product

Sources & evidence

ORD record
ord-02d98d6845c7439b9cc32c1ad5f1b3a9
Source dataset
uspto-grants-1990_07
Patent number
US04940654

Reaction notes

Loading…