Diethyl Oxalate → HCID 19100688, compound

HRID 1974999Notes

Reaction equation

HRID 1974999 reaction equation
C([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:22]#[N:23])=[CH:11][S:12][C:13]=1[NH:14][C:15](OC(C)(C)C)=[O:16])=O)(C)(C)C.C(OC(=O)C(OCC)=O)C>C(O)(=O)C>[C:22]([C:10]1[C:9]2[NH:8][C:6](=[O:5])[C:15](=[O:16])[NH:14][C:13]=2[S:12][CH:11]=1)#[N:23]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 53762396HCID 53762396, compound

Product 1

HCID 19100688HCID 19100688, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-bis(t-butoxycarbonyl)amino-5-t-butoxycarbonylamino-3-thiophene carbonitrile (15.4 g, 35 mmol), diethyloxalate (100 ml, 739 mmol) and glacial acetic acid (100 ml) was refluxed for 6 h. The crystallinic product was filtered off and washed with ether to give 3.25 9 (48%) of the title compound. M.p.>250° C. 1H-NMR (DMSO-d6, δ): 8.15 (s, 1H), 12.4 (br.s, 1H), 12.5 (br.s, 1H).

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationThe crystallinic product was filtered off
  3. washwashed with ether

Sources & evidence

ORD record
ord-e749da0b473e444993ba129f7c7e0234
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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