HCID 19100702, compound → HCID 23186987, compound

HRID 1974993Notes

Reaction equation

HRID 1974993 reaction equation
[CH2:1]([C:3]1[C:4]([NH:17][C:18]([O:20]C(C)(C)C)=O)=[C:5]([NH:9][C:10](OC(C)(C)C)=[O:11])[S:6][C:7]=1[CH3:8])[CH3:2]>C(O)(=O)C.C(OCC)(=O)C(OCC)=O>[CH2:1]([C:3]1[C:4]2[NH:17][C:18](=[O:20])[C:10](=[O:11])[NH:9][C:5]=2[S:6][C:7]=1[CH3:8])[CH3:2]

Participants

4

Reactant 1

HCID 19100702HCID 19100702, compound

Product 1

HCID 23186987HCID 23186987, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7268Diethyl OxalateSolvent

Procedure

4.5 g of crude di-t-butyl 4-ethyl-5-methylthiophene-2,3-dicarbamate was dissolved in a mixture of 30 ml of acetic acid and 30 ml of diethyl oxalate, and refluxed for six hours. Upon cooling to room temperature, the crystalline precipitate was isolated (900 mg). Recrystallisation from hot acetic acid combined with charcoal (Norit SU 18) yielded 660 mg of the title compound, m.p.>300° C. MS: 210. 1H-NMR (DMSO-d6, δ): 1.0 (t, 3H), 2.2 (s, 3H), 2.6 (q, 2H), 11.9 (br.s, 1H), 12.1 (br.s, 1H).

Workup

  1. temperaturerefluxed for six hours
  2. customthe crystalline precipitate was isolated (900 mg)
  3. customRecrystallisation from hot acetic acid

Sources & evidence

ORD record
ord-93c70efe30c5483b87c6d62d2b4b7e59
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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