Tetrahydrofuran → 5-(4-Methoxyphenyl)-1,3,4-oxathiazol-2-one

HRID 240810Notes

Reaction equation

HRID 240810 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1.Cl[S:13]Cl.C1[CH2:19][O:18]CC1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[O:8][C:19](=[O:18])[S:13][N:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 25353Sulfur dichlorideHCID 769594-Methoxybenzamide

Product 1

HCID 8194565-(4-Methoxyphenyl)-1,3,4-oxathiazol-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

4-Methoxybenzamide (3.0 g, 19.9 mmol) was suspended in a mixture of toluene (30 mL) and THF (15 mL), and chlorosulfenyl chloride (3.35 mL, 39.7 mmol) was then added to the suspension. The obtained mixture was stirred at 80° C. for 2.5 hours. The reaction solution was cooled to room temperature, and it was then concentrated under reduced pressure. Thereafter, diethyl ether was added to the residue, and insoluble materials were then removed by filtration, so as to obtain the title compound (3.64 g, 88%) in the form of a colorless solid.

Workup

  1. additionwas then added to the suspension
  2. temperatureThe reaction solution was cooled to room temperature
  3. concentrationit was then concentrated under reduced pressure
  4. additionThereafter, diethyl ether was added to the residue, and insoluble materials
  5. customwere then removed by filtration

Sources & evidence

ORD record
ord-a94f5d3b2c354ec1b946040e641dba93
Source dataset
uspto-grants-2014_02
Patent number
US08648103B2

Reaction notes

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