1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19787203, compound

HRID 1885203Notes

Reaction equation

HRID 1885203 reaction equation
C1CCN2C(=NCCC2)CC1.[Cl:12][C:13]1[CH:36]=[CH:35][CH:34]=[CH:33][C:14]=1[C:15]([C:17]1[CH:21]=[C:20]([CH2:22][CH3:23])[S:19][C:18]=1[NH:24][C:25](=[O:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=O>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:36]=[CH:35][CH:34]=[CH:33][C:14]=1[C:15]1[C:17]2[CH:21]=[C:20]([CH2:22][CH3:23])[S:19][C:18]=2[NH:24][C:25](=[O:32])[C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19787202HCID 19787202, compound

Product 1

HCID 19787203HCID 19787203, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of DBU (5.2 g) in toluene (50 ml) was added dropwise a solution of 3-(2-chlorobenzoyl)-2-ethoxycarbonylacetylamino-5-ethylthiophene (6.5 g) in toluene (30 ml) over one hour with stirring under reflux. After refluxing for 7 hours, the mixture was washed with water and dried over MgSO4, and then the solvent was distilled off. The residue was chromatographed on a silica gel column and eluted with hexane-acetone (5 : 1). The solvent was distilled off and hexane was added to obtain ethyl 4-(2-chlorophenyl)-6,7-dihydro-2-ethyl-6-oxothieno[2,3-b]pyridine-5-carboxylate as crystals 33.1%). The crystals were recrystallized from ethanol to obtain light yellow prisms, mp: 126°-127° C.

Workup

  1. temperatureunder reflux
  2. temperatureAfter refluxing for 7 hours
  3. washthe mixture was washed with water
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off
  6. customThe residue was chromatographed on a silica gel column
  7. washeluted with hexane-acetone (5 : 1)
  8. distillationThe solvent was distilled off
  9. additionhexane was added

Sources & evidence

ORD record
ord-0cf6bdde412c475aa4dd6ca8b97163e9
Source dataset
uspto-grants-1992_09
Patent number
US05143919

Reaction notes

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