2-Propenamide, 3-phenyl- → HCID 13021992, compound

HRID 967757Notes

Reaction equation

HRID 967757 reaction equation
[C:1]([NH2:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:13]([S:15]Cl)=[O:14]>C(Cl)(Cl)Cl>[C:4]1(/[CH:3]=[CH:2]/[C:1]2[O:10][C:13](=[O:14])[S:15][N:11]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 121352-Propenamide, 3-phenyl-HCID 75990(Chlorothio)formyl chloride

Product 1

HCID 13021992HCID 13021992, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Cinnamamide (1.9 g, 13 mmol) was mixed with chlorocarbonylsulphenylchloride (1.0 mL, 13 mmol) in chloroform and heated to reflux for 18 h. The reaction mixture was concentrated in vacuo and the resultant material was taken up in boiling hexane (100 mL). The solvent was decanted from the remaining solid, the volume of this solution was reduced by half, and the solution was allowed to cool. The crystalline solids which formed were collected and washed with hexane to afford 5-[(E)-2-phenylethenyl]-1,3,4-oxathiazol-2-one (1.93 g, 72% yield) as pale yellow needles. M.p. 105–106° C. 1H NMR (DMSO-d6, 300 MHz) δ 7.52 (m, 3H), 7.46 (s, 0.5H), 7.41 (m, 2.5H), 6.63 (d, J=16 Hz, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe solvent was decanted from the remaining solid
  5. temperatureto cool
  6. customThe crystalline solids which formed
  7. customwere collected
  8. washwashed with hexane

Sources & evidence

ORD record
ord-ceb2340d75d74d36b0f586dd55748519
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

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