HCID 19100694, compound → HCID 19100696, compound

HRID 1974996Notes

Reaction equation

HRID 1974996 reaction equation
O.Br[C:3]1[S:13][C:6]2[NH:7][C:8](=[O:12])[C:9](=[O:11])[NH:10][C:5]=2[C:4]=1[Br:14]>C(O)(=O)C.[Zn]>[Br:14][C:4]1[C:5]2[NH:10][C:9](=[O:11])[C:8](=[O:12])[NH:7][C:6]=2[S:13][CH:3]=1

Participants

4

Reactant 1

HCID 19100694HCID 19100694, compound

Product 1

HCID 19100696HCID 19100696, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

6,7-Dibromothieno[2,3-b]pyrazine-2,3(1H,4H)-dione hydrate (0.50 g, 1.45 mmol) was dissolved in 113 ml 97% acetic acid at 100° C. and 0.11 g (1.68 mmol) of zinc dust was added in one portion. After stirring 24 h another 0.11 g (1.68 mmol) of zinc dust was added and the stirring was continued at 100° C. for 24 h. The reaction mixture was filtrated and evaporated to dryness under reduced pressure and 10 ml of water was added. The precipitate was filtered off and washed with water and dried. The crude material (0.215 g) was recrystallized from acetic acid to afford 0.104 g (29%) of the title compound. M.p. 295°-296° C. 1H-NMR (DMSO-D6, δ): 7.3 (s, 1H), 11.9 (s, 1H), 12.35 (s, 1H).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtrated
  3. customevaporated to dryness under reduced pressure and 10 ml of water
  4. additionwas added
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customdried
  8. customThe crude material (0.215 g) was recrystallized from acetic acid

Sources & evidence

ORD record
ord-a0c1161cb5344955a4abb7c02a6a0075
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

Loading…