Diethyl Oxalate → HCID 19100711, compound

HRID 1974978Notes

Reaction equation

HRID 1974978 reaction equation
[CH:1]([C:4]1[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]=1)([CH3:3])[CH3:2].C(OCC)(=O)C(OCC)=O>C(O)(=O)C>[CH:1]([C:4]1[C:5]2[NH:17][C:18](=[O:20])[C:10](=[O:11])[NH:9][C:6]=2[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 19100786HCID 19100786, compound

Product 1

HCID 19100711HCID 19100711, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of di-t-butyl 4-isopropylthiophene-2,3-dicarbamate (1.42 g, 3.98 mmol), diethyl oxalate (25 ml, 183 mmol) and glacial acetic acid (25 ml) was refluxed for 2 h. The reaction mixture was cooled on ice for 2 h and the precipitate was filtered off, washed twice with water and finally with ether. Yield 580 mg (69%) of the title compound. M.p.>250° C. 1H-NMR (DMSO-D6, δ) 1.15 (d, 6H), 3.1 (m, 1H), 6.75 (s, 1H), 11.9 (br.s, 2H). MS (70 eV): m/z 210 (100%, g), 195 (97), 182 (42), 167 (52), 154 (12), 139 (29), 122 (13), 97 (19).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperatureThe reaction mixture was cooled on ice for 2 h
  3. filtrationthe precipitate was filtered off
  4. washwashed twice with water and finally with ether

Sources & evidence

ORD record
ord-41794aa5009444a5a76b4983dc235213
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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