Diethyl Ether → HCID 13796806, compound

HRID 1029365Notes

Reaction equation

HRID 1029365 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH2:11][CH3:12])=[N:7][C:6]=2[CH:13]=1.[C:14]1([CH3:26])[CH:19]=[CH:18][C:17]([S:20]([O:23]CC)(=[O:22])=[O:21])=[CH:16][CH:15]=1.[CH3:27][CH2:28]OCC>CC(C)=O>[S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:26])=[CH:15][CH:16]=1)([O-:23])(=[O:22])=[O:21].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH2:11][CH3:12])=[N+:7]([CH2:27][CH3:28])[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6638Ethyl p-methylbenzenesulfonateHCID 784990HCID 784990, compound

Product 1

HCID 13796806HCID 13796806, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Chloro-2-(ethylthio)benzothiazole (11.5 g, 0.05 mol) and 10.55 g ethyl p-toluenesulfonate were heated at 150°-160° C. for 2 hours. After cooling, the product was dissolved in acetone and poured into 400 ml stirred anhydrous ether. The resulting precipitated oil crystallized upon scraping with a spatula. The ether was decanted, the solid triturated with ether, and the ether again decanted to yield 11.04 g (51%) after air drying.

Workup

  1. temperatureAfter cooling
  2. additionpoured into 400 ml
  3. customThe resulting precipitated oil
  4. customcrystallized
  5. customThe ether was decanted
  6. customthe solid triturated with ether
  7. customthe ether again decanted
  8. customto yield 11.04 g (51%) after air
  9. customdrying

Sources & evidence

ORD record
ord-4383754803754e959a87b2f8ec18768c
Source dataset
uspto-grants-1992_04
Patent number
US05102781

Reaction notes

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