Lawesson's reagent → HCID 13934592, compound

HRID 2118732Notes

Reaction equation

HRID 2118732 reaction equation
[C:1]1([N:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[O:17][CH2:18][CH2:19][C:9]=3[C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:30]2)=CC=1>C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[O:17][CH2:18][CH2:19][C:9]=3[C:8]2=[S:30])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 13934590HCID 13934590, compound

Product 1

HCID 13934592HCID 13934592, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3,5-dihydro-5-phenyl-furo-[3,2-c][1,8]naphthyridin-4(2H)-one (3 g.) and 2,4-bis- (4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's Reagent; 5 g.) in dry toluene (100 ml.) was stirred in an atmosphere of nitrogen and heated to reflux for 6 hrs. After cooling, the organic layer was washed with water, dried and evaporated. The product was purified by chromatography over silica gel in CH2Cl2 containing increasing amounts of ethyl acetate (0-5%). The fractions containing pure product were combined, evaporated, suspended in ethanol, filtered and dried to yield the desired product, m.p. 242°-244.5° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hrs
  3. temperatureAfter cooling
  4. washthe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. customThe product was purified by chromatography over silica gel in CH2Cl2 containing
  8. temperatureincreasing amounts of ethyl acetate (0-5%)
  9. additionThe fractions containing pure product
  10. customevaporated
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-0b7f9657e6fa40faa1eaa0ac2d5fc398
Source dataset
uspto-grants-1987_07
Patent number
US04680298

Reaction notes

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