Diethyl Oxalate → HCID 19100721, compound

HRID 1974985Notes

Reaction equation

HRID 1974985 reaction equation
[CH:1]1([C:7]2[C:8]([NH:20][C:21]([O:23]C(C)(C)C)=O)=[C:9]([NH:12][C:13](OC(C)(C)C)=[O:14])[S:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(OCC)(=O)C(OCC)=O>C(O)(=O)C>[CH:1]1([C:7]2[C:8]3[NH:20][C:21](=[O:23])[C:13](=[O:14])[NH:12][C:9]=3[S:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 19100744HCID 19100744, compound

Product 1

HCID 19100721HCID 19100721, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of di-t-butyl 4-cyclohexylthiophene-2,3-dicarbamate (400 mg, 1mmol), diethyl oxalate (5 ml, 37 mmol) and glacial acetic acid (5 ml) was refluxed for 16 h. The precipitate was filtered off and washed with glacial acetic acid to give 60 mg (24%) of the title compound. M.p.>270° C. 1H-NMR (DMSO-d6, δ): 1.1-1.9 (m, 10H), 2.75 (m, 1H), 6.7 (s, 1H), 11.9 (s, 1H), 12.25 (s, 1H).

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationThe precipitate was filtered off
  3. washwashed with glacial acetic acid

Sources & evidence

ORD record
ord-56a01dc1dd0747628b5db7c7635e6a7f
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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