4-Fluorobenzamide → HCID 14087130, compound

HRID 2274855Notes

Reaction equation

HRID 2274855 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Cl[C:12]([S:14]Cl)=[O:13]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][C:12](=[O:13])[S:14][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 715724-FluorobenzamideHCID 75990(Chlorothio)formyl chloride

Product 1

HCID 14087130HCID 14087130, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of 4-fluorobenzamide (70.00 g, 503.1 mmol) in toluene (900 mL) was added chlorocarbonyl sulfenyl chloride (83.0 mL, 1.00 mol). The mixture was heated overnight at 60° C. and concentrated. The resulting tan solid was triturated with methylene chloride (200 mL), collected by suction filtration and rinsed with additional methylene chloride (4×70 mL). The crude product was impregnated onto silica (100 g) and chromatographed in a large filter funnel dry loaded with silica using a hexane/ethyl acetate gradient. The product 5(4-fluorophenyl)-1,3,4-oxathiazol-2-one was afforded as an off-white solid (55.98 g, 56%).

Workup

  1. concentrationconcentrated
  2. customThe resulting tan solid was triturated with methylene chloride (200 mL)
  3. filtrationcollected by suction filtration
  4. washrinsed with additional methylene chloride (4×70 mL)
  5. customchromatographed in a large filter funnel
  6. customdry

Sources & evidence

ORD record
ord-123915f3b0c948f79f91c0c4ff3cc45e
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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