HCID 82371923, compound → HCID 54105850, compound

HRID 440276Notes

Reaction equation

HRID 440276 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][C:10]=1[OH:11])=[O:5])[CH3:2].C(N=C(O)N(C(C)C)[C:21]([CH3:24])([CH3:23])[CH3:22])(C)C>C(Cl)Cl>[C:21]([O:11][C:10]1[CH:9]=[C:8]([C:12]([O:14][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:13])[S:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 82371923HCID 82371923, compoundHCID 178457940HCID 178457940, compound

Product 1

HCID 54105850HCID 54105850, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl-3-hydroxy-5-carboxy-2-thiophenecarboxylate(25 g, 0.115 mmol) in dry (25 g, 0.115 mmol) in dry CH2Cl2 (200 ml) was treated, at ambient temperature, with diisopropyl-tert-butylisourea (175 ml) added dropwise. This caused an exotherm which heated the mixture to reflux. The reaction mixture was then stirred for 12 hours, the solid removed by filtration, and the CH2Cl2 evaporated. The residual oil was purified by subjecting to silica gel chromatography, eluting with petroleum ether: ether (90:10) to give a mixture of two products (28.5 g). These two products were separated by flash chromatography, eluting with CH2Cl2 : petroleum ether (1:1), to give title compound (12.6 g, 33%).

Workup

  1. additionadded dropwise
  2. temperatureheated the mixture
  3. temperatureto reflux
  4. customthe solid removed by filtration
  5. customthe CH2Cl2 evaporated
  6. customThe residual oil was purified
  7. washeluting with petroleum ether: ether (90:10)
  8. customto give
  9. customThese two products were separated by flash chromatography
  10. washeluting with CH2Cl2 : petroleum ether (1:1)

Sources & evidence

ORD record
ord-dc1da120256f4ac69d88a944b6b119d4
Source dataset
uspto-grants-1996_05
Patent number
US05519015

Reaction notes

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