Diethyl Oxalate → Thieno[2,3-b]pyrazine-2,3(1H,4H)-dione

HRID 1974959Notes

Reaction equation

HRID 1974959 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7](OC(C)(C)C)=[O:8])=[C:2]1[NH:14][C:15]([O:17]C(C)(C)C)=O.C(OCC)(=O)C(OCC)=O>C(O)(=O)C>[NH:6]1[C:7](=[O:8])[C:15](=[O:17])[NH:14][C:2]2[S:1][CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 13580615HCID 13580615, compound

Product 1

HCID 19100709Thieno[2,3-b]pyrazine-2,3(1H,4H)-dioneYield 78.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of di-t-butyl thiophene-2,3-dicarbamate (1.53 g, 4.87 mmol), diethyl oxalate (15 ml) and acetic acid (15 ml) was refluxed for 48 hours. The precipitate was filtered off, washed with water and dried to yield 0.64 g (78%) of the title compound. M.p. >340° C. 1H-NMR (DMSO-d6, δ): 6.74 (d, 1H), 7.13 (d, 1H), 12.28 (s, 1H).

Workup

  1. temperaturewas refluxed for 48 hours
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-641f15be9ad14c66bd62c2230aecea1a
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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