Alloxan → HCID 12962677, compound

HRID 1262932Notes

Reaction equation

HRID 1262932 reaction equation
C(OC(C)C)(C)C.C([Li])CCC.CCCCCC.Br[C:20]1[CH:24]=[CH:23][S:22][CH:21]=1.[NH:25]1[C:33](=[O:34])[C:31](=[O:32])[C:29](=[O:30])[NH:28][C:26]1=[O:27]>O1CCCC1>[OH:32][C:31]1([C:20]2[CH:24]=[CH:23][S:22][CH:21]=2)[C:29](=[O:30])[NH:28][C:26](=[O:27])[NH:25][C:33]1=[O:34]

Participants

7

Reactant 5

HCID 5781AlloxanHCID 7914Diisopropyl EtherHCID 8058HexaneHCID 133833-BromothiopheneHCID 178418339Butyllithium

Product 1

HCID 12962677HCID 12962677, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

Isopropyl ether (40 ml.) was cooled to -70° C. Butyl lithium in hexane (2.4 M, 10 ml., 24 mmoles) was added over 10 minutes, keeping the temperature -70° to -60° C. 3-Bromothiophene (1.9 ml., 20 mmoles) was added over 20 minutes, keeping the temperature -72° to -68° C. The mixture was stirred for an additional 30 minutes at -72° to 70° C. Sublimed alloxan (3 g., 21 mmoles) in 25 ml. of tetrahydrofuran was added over 40 minutes, keeping the temperature -70° to -65° C. Stirring at this temperature was continued for 15 minutes. The cooling bath was removed and the reaction mixture stirred for one hour at room temperature, then cooled to 5° C. Hydrochloric acid (1 N, 40 ml.) was added slowly, and the organic phase separated. The aqueous phase was extracted with 35 ml. of ethyl acetate. The combined organic phase/extract was washed with 10 ml. of water, dried over anhydrous sodium sulfate and concentrated to yield solid 5-hydroxy-5-(3-thienyl)-2,4,6(1H,3H,5H)pyrimidinetrione (1.41 g., 31%; m/e 226).

Workup

  1. customthe temperature -70° to -60° C
  2. customthe temperature -72° to -68° C
  3. customthe temperature -70° to -65° C
  4. stirringStirring at this temperature
  5. waitwas continued for 15 minutes
  6. customThe cooling bath was removed
  7. stirringthe reaction mixture stirred for one hour at room temperature
  8. additionHydrochloric acid (1 N, 40 ml.) was added slowly
  9. customthe organic phase separated
  10. extractionThe aqueous phase was extracted with 35 ml
  11. extractionThe combined organic phase/extract
  12. washwas washed with 10 ml
  13. dry with materialof water, dried over anhydrous sodium sulfate
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-dacf0699df8440b6abc7e0f6268a2fb1
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

Loading…