Thionyl Chloride → HCID 10589352, compound

HRID 649023Notes

Reaction equation

HRID 649023 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:19]=[C:18]2[C:9]([S:10](=[O:25])(=[O:24])[C:11]3[CH:12]=[C:13]([C:21]([NH2:23])=O)[CH:14]=[CH:15][C:16]=3[C:17]2=[O:20])=[CH:8][CH:7]=1>CN(C=O)C>[C:21]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[C:17](=[O:20])[C:18]1[CH:19]=[C:6]([F:5])[CH:7]=[CH:8][C:9]=1[S:10]2(=[O:25])=[O:24])#[N:23]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20144443HCID 20144443, compound

Product 1

HCID 10589352HCID 10589352, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (75 g) was cooled to 5° C. and DMF (150 ml) was added dropwise and the temperature was maintained below 10° C. The amide prepared in (a) supra, 19.1 g, (0.05 mol) was added and the mixture was allowed to warm to room temperature and was stirred for 2 hr. The mixture was poured onto 1 L of ice and was filtered. The solid was washed with H2O, 2×300 ml and dried. The nitrile was dissolved in hot acetic acid (800 ml), treated with charcoal and filtered through a celite bed. The solution was cooled, and the crystals were collected by filtration and dried in vacuo to give 14.48 g of 6-cyano-2-fluorothioxanthene-9-one 10,10-dioxide, m.p.=260°-262°0 C.; TLC on silica gel (butanol:acetic acid:H2O/5:4:1), Rf =0.82.

Workup

  1. temperaturethe temperature was maintained below 10° C
  2. additionwas added
  3. filtrationwas filtered
  4. washThe solid was washed with H2O, 2×300 ml
  5. customdried
  6. dissolutionThe nitrile was dissolved in hot acetic acid (800 ml)
  7. additiontreated with charcoal
  8. filtrationfiltered through a celite bed
  9. temperatureThe solution was cooled
  10. filtrationthe crystals were collected by filtration
  11. customdried in vacuo

Sources & evidence

ORD record
ord-95b8253fd2bf405d8fea776e552b0d0c
Source dataset
uspto-grants-1988_04
Patent number
US04737514

Reaction notes

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