Triphenylphosphine → HCID 14770039, compound

HRID 1109568Notes

Reaction equation

HRID 1109568 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][CH2:33][CH2:34][NH:35][C:36]([C:38]1[CH:39]=[C:40]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:41](=[O:51])[N:42]2[C:47]=1[C:46]1[S:48][CH:49]=[CH:50][C:45]=1[CH2:44][CH2:43]2)=O>O1CCCC1>[O:32]1[CH2:33][CH2:34][N:35]=[C:36]1[C:38]1[CH:39]=[C:40]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:41](=[O:51])[N:42]2[C:47]=1[C:46]1[S:48][CH:49]=[CH:50][C:45]=1[CH2:44][CH2:43]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 14770051HCID 14770051, compound

Product 1

HCID 14770039HCID 14770039, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.94 g of diethyl azodicarboxylate and 0.71 g of triphenylphosphine were added to a solution of 1.0 g of 4,5-dihydro-N-(2-hydroxyethyl) -8-phenyl-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxamide in 27 ml of tetrahydrofuran, whereupon the reaction mixture was stirred for 24 hours. The mixture was then evaporated in vacuo, the residue was treated with water and extracted three times with methylene chloride. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel with acetonitrile/diethyl ether (2:3). By recrystallization from dioxane, there was obtained 4,5-dihydro-10-(2-oxazolin-2-yl)-8-phenyl-7H-thieno[2,3-a]quinolizin-7-one of m.p. 211°-212°.

Workup

  1. customThe mixture was then evaporated in vacuo
  2. additionthe residue was treated with water
  3. extractionextracted three times with methylene chloride
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel with acetonitrile/diethyl ether (2:3)
  7. customBy recrystallization from dioxane

Sources & evidence

ORD record
ord-43501d65e93d4b03bb0638ae905450a0
Source dataset
uspto-grants-1994_06
Patent number
US05321021

Reaction notes

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