2-Fluorobenzamide → HCID 12437393, compound

HRID 1956128Notes

Reaction equation

HRID 1956128 reaction equation
Cl[C:2]([S:4]Cl)=[O:3].[F:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10]>C1(C)C=CC=CC=1>[F:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]1[O:10][C:2](=[O:3])[S:4][N:11]=1

Participants

4

Reactant 2

HCID 679642-FluorobenzamideHCID 75990(Chlorothio)formyl chloride

Product 1

HCID 12437393HCID 12437393, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Chlorocarbonyl sulfenyl chloride (11.24 g, 86 mmol) is added dropwise to a stirred suspension of 2-fluorobenzamide (10.80 g, 78 mmol) in dry toluene. The mixture is heated gradually over a period of 30 minutes to a temperature of about 80° C. (a clear solution is formed with evolution of gas), stirred for approximately 1 h at 80° C., heated to about 98° C., stirred at 98° C. for 5 h, and distilled to remove the toluene and excess chlorocarbonyl sulfenyl chloride. The resultant pot residue is redissolved in toluene, washed sequentially with water, 5% sodium bicarbonate and water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a residue. This residue is recrystallized from petroleum ether to give 5-(2-fluorophenyl)[1,3,4]oxathiazolin-2-one (13.2 g, 86%) as off-white crystals, mp 50° C.

Workup

  1. customis formed with evolution of gas),
  2. temperatureheated to about 98° C.
  3. stirringstirred at 98° C. for 5 h
  4. distillationdistilled
  5. customto remove the toluene and excess chlorocarbonyl sulfenyl chloride
  6. dissolutionThe resultant pot residue is redissolved in toluene
  7. washwashed sequentially with water, 5% sodium bicarbonate and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto give a residue
  11. customThis residue is recrystallized from petroleum ether

Sources & evidence

ORD record
ord-75497ebc1c6d46a0b796e5fd0fd8aeb9
Source dataset
uspto-grants-1998_07
Patent number
US05780393

Reaction notes

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