Diethyl Oxalate → HCID 19100723, compound

HRID 1974981Notes

Reaction equation

HRID 1974981 reaction equation
[CH:1]1([C:4]2[C:5]([NH:17][C:18]([O:20]C(C)(C)C)=O)=[C:6]([NH:9][C:10](OC(C)(C)C)=[O:11])[S:7][CH:8]=2)[CH2:3][CH2:2]1.C(OCC)(=O)C(OCC)=O>C(O)(=O)C>[CH:1]1([C:4]2[C:5]3[NH:17][C:18](=[O:20])[C:10](=[O:11])[NH:9][C:6]=3[S:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 19100804HCID 19100804, compound

Product 1

HCID 19100723HCID 19100723, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of di-t-butyl 4-cyclopropylthiophene-2,3-dicarbamate (1.66 g, 4.7 mmol), diethyl oxalate (20 ml, 146 mmol) and glacial acetic acid (20 ml) was refluxed for 12 h. The mixture was concentrated in vacuo and the residue recrystallized from glacial acetic acid to afford 460 mg (72%) of the title compound. M.p.>250° C. 1H-NMR (DMSO-d6, δ): 0.6 (m, 2H), 0.85 (m, 2H), 2.0 (m, 1H), 6.55 (s, 1H), 12.0 (s, 1H), 12.2 (s, 1H).

Workup

  1. temperaturewas refluxed for 12 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue recrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-4659745ae5fb4398aab23683e26a5963
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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