Diethyl Oxalate → HCID 178470315, compound

HRID 131203

Reaction equation

HRID 131203 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH2:9])=[O:8].CC[O-].[Na+].[CH2:14]([O:16][C:17](=[O:23])[C:18](OCC)=O)[CH3:15]>CCO>[OH:8][C:7]1[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[N:1]=[C:18]([C:17]([O:16][CH2:14][CH3:15])=[O:23])[N:9]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 5189933-Aminothiophene-2-carboxamideHCID 2723922Sodium ethoxide

Product 1

HCID 178470315HCID 178470315, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-aminothiophene-2-carboxamide (1.23 g, 8.65 mmol) and EtOH (25 mL) was treated with NaOEt (1.2 g, 17.3 mmol) and diethyloxalate (2.3 mL, 17.3 mmol), refluxed for 18 h, cooled, concentrated in vacuo, treated with water, acidified with HOAc and filtered to give the title compound (1.43 g, 74%) as a cream solid: IR νmax Nujol)/cm−1 3180, 3119, 3078, 3006, 2955, 2924, 2854, 1737, 1667, 1651, 1300 and 1176; NMR δH (400 MHz, DMSO) 1.37 (3H, t, J 7.0 Hz), 4.40 (2H, q, J 7.0 Hz), 7.58 (1H, d, J 5.0 Hz), 8.30 (1H, d, J 5.1 Hz), and 12.92 (1H, s).

Workup

  1. temperaturerefluxed for 18 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. additiontreated with water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-18e76db551d84be996568917ff3e1d18
Source dataset
uspto-grants-2008_06
Patent number
US07384949B2

Linked notes

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