Ammonia → HCID 10215378, compound

HRID 747834Notes

Reaction equation

HRID 747834 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[C:6]1([N:12]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][C:16](=[O:17])[NH:15][C:13]2=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH3:26]>C(Cl)(Cl)Cl.O1CCCC1.C(OC(=O)C)C>[O:14]=[C:13]1[N:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:19]([C:20]2[CH:21]=[CH:22][C:23]([S:2]([NH2:26])(=[O:5])=[O:3])=[CH:24][CH:25]=2)=[CH:18][C:16](=[O:17])[NH:15]1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 24638Chlorosulfonic acidHCID 135667411,6-Diphenylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 10215378HCID 10215378, compoundYield 18.3%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The chlorosulfonic acid (1.18 g, 10 mmol) was added to a solution of 1,6-diphenyluracil (0.2 g, 0.75 mmol) (synthesized according to the procedure given in Harvey I. Skulnick, Heterocycles, 23, (7), pp 1685, 1985) in chloroform (20 ml) and refluxed for 2 hours. The reaction mixture was poured onto ice-water mixture and extracted with ethylacetate. The ethylacetate extract was washed with brine, dried over anhydrous sodium sulphate and concentrated to dryness under reduced pressure. The crude solid thus obtained was taken in tetrahydrofuran (20 ml) and treated with ammonia solution (1 ml) under stirring. The reaction mixture was stirred for 1 hour and concentrated to dryness in vacuum. The product thus obtained was dissolved in ethylacetate, washed with water, brine and dried over anhydrous sodium sulphate. The ethylacetate extract was concentrated to dryness under reduced pressure and purified by column chromatography to yield the title compound (0.1 g, 18.3%). mp: ______.

Workup

  1. customsynthesized
  2. additionThe reaction mixture was poured onto ice-water mixture
  3. extractionextracted with ethylacetate
  4. extractionThe ethylacetate extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe crude solid thus obtained
  9. stirringThe reaction mixture was stirred for 1 hour
  10. concentrationconcentrated to dryness in vacuum
  11. customThe product thus obtained
  12. washwashed with water, brine
  13. dry with materialdried over anhydrous sodium sulphate
  14. extractionThe ethylacetate extract
  15. concentrationwas concentrated to dryness under reduced pressure
  16. custompurified by column chromatography

Sources & evidence

ORD record
ord-9f7ef76b73554aff88514ae6307b8798
Source dataset
uspto-grants-2008_07
Patent number
US07399760B2

Reaction notes

Loading…