Diethyl Oxalate → HCID 19100727, compound

HRID 1974983Notes

Reaction equation

HRID 1974983 reaction equation
[CH2:1]([C:5]1[C:6]([NH:18][C:19]([O:21]C(C)(C)C)=O)=[C:7]([NH:10][C:11](OC(C)(C)C)=[O:12])[S:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3].C(OCC)(=O)C(OCC)=O>C(O)(=O)C>[CH2:1]([C:5]1[C:6]2[NH:18][C:19](=[O:21])[C:11](=[O:12])[NH:10][C:7]=2[S:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 19100762HCID 19100762, compound

Product 1

HCID 19100727HCID 19100727, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of di-t-butyl 4-isobutylthiophene-2,3-dicarbamate (3.70 g, 10 mmol), diethyl oxalate (30 ml, 220 mmol) and glacial acetic acid (30 ml) was refluxed for 20h. The mixture was concentrated and the residue was recrystallized from aqueous acetic acid to afford 1.4 g (62.5%) of the title compound. M.p.>270° C. 1H-NMR (DMSO-d6, δ): 0-9 (d, 6H), 1.75 (m, 1H), 2.45 (d, 2H), 6.75 (s, 1H), 11.9 (s, 1H), 12.2 (br.s, 1H).

Workup

  1. temperaturewas refluxed for 20h
  2. concentrationThe mixture was concentrated
  3. customthe residue was recrystallized from aqueous acetic acid

Sources & evidence

ORD record
ord-16e32b58ec004f418fcad3279d0a4e9f
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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