Phosphoric Acid → HCID 12756957, compound

HRID 1389283Notes

Reaction equation

HRID 1389283 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[C:4]([S:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH:3]=1.P(=O)(O)(O)O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[CH2:8][C:9](=[O:11])[C:14]3[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=3[S:12][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14812Phosphorus oxide (P4O10)HCID 12756952HCID 12756952, compound

Product 1

HCID 12756957HCID 12756957, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[4-Fluoro-2-(4-nitrophenylthio)phenyl]acetic acid (17.6 g) was added at 150° C. to polyphosphoric acid, prepared from 60 ml 85% phosphoric acid and 100 g phosphorus pentoxide, and the mixture stirred at 150°-155° C. for two hours. After cooling, it was decomposed by pouring into a mixture of ice and water. The precipitated crude product was filtered and boiled for a short time under stirring with a mixture of a 10% sodium carbonate solution and benzene. It was filtered again, the benzene layer separated and benzene evaporated. The residue was dissolved in a small volume of benzene and the solution chromatographed on a column of 420 g alumina (act. II) Benzene eluted first a small amount of a less polar and high-melting by-product. The elution was continued with benzene and finally with a mixture of benzene and chloroform; 7.25 g of the desired crystalline 3-fluoro-8-nitrodibenzo(b,f)thiepin-10(11H)-one were obtained, m.p. 161°-163° C. (benzene-petroleum ether).

Workup

  1. temperatureAfter cooling
  2. customThe precipitated crude product
  3. filtrationwas filtered
  4. stirringunder stirring with a mixture of a 10% sodium carbonate solution and benzene
  5. filtrationIt was filtered again
  6. customthe benzene layer separated
  7. custombenzene evaporated
  8. dissolutionThe residue was dissolved in a small volume of benzene
  9. customthe solution chromatographed on a column of 420 g alumina (act. II) Benzene
  10. washeluted first a small amount of a less polar and high-melting by-product
  11. washThe elution
  12. additionwas continued with benzene and finally with a mixture of benzene and chloroform

Sources & evidence

ORD record
ord-b1c1db45a1d745b38e0734108174b644
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

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