Phthalimide → HCID 19973561, compound

HRID 1736480Notes

Reaction equation

HRID 1736480 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[Cl:32][C:33]1[CH:34]=[C:35]([CH:39](O)[CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[CH:36]=[CH:37][CH:38]=1.[C:48]1(=[O:58])[NH:52][C:51](=[O:53])[C:50]2=[CH:54][CH:55]=[CH:56][CH:57]=[C:49]12>O1CCCC1>[Cl:32][C:33]1[CH:34]=[C:35]([CH:39]([N:52]2[C:51](=[O:53])[C:50]3=[CH:54][CH:55]=[CH:56][CH:57]=[C:49]3[C:48]2=[O:58])[CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12857973HCID 12857973, compound

Product 1

HCID 19973561HCID 19973561, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-30 °C

Procedure

70 ml of a solution of 16.5 g of triphenylphosphine in tetrahydrofuran was cooled to -50° C., followed by the gradual dropwise addition thereto of 40 ml of a solution of 11.0 g of diethyl azodicarboxylate in tetrahydrofuran. The obtained mixture was stirred at -30° C. for 30 minutes, followed by the dropwise addition thereto of 50 ml of a tetrahydrofuran solution of 13.4 g of the 1-(3-chlorophenyl)-2-(pyridin-2-yl)ethyl alcohol prepared in the Preparative Example 19. The obtained mixture was stirred at that temperature for 30 minutes, followed by the addition thereto of 9.28 g of phthalimide. The obtained mixture was stirred at room temperature for 30 minutes and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to column chromatography and eluted with a toluene/ethyl acetate mixture. Yield: 12.9 g.

Workup

  1. additionfollowed by the gradual dropwise addition
  2. additionfollowed by the dropwise addition
  3. stirringThe obtained mixture was stirred at that temperature for 30 minutes
  4. additionfollowed by the addition
  5. stirringThe obtained mixture was stirred at room temperature for 30 minutes
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. washeluted with a toluene/ethyl acetate mixture

Sources & evidence

ORD record
ord-f5351bdbe5884a2393aa06beec798aaa
Source dataset
uspto-grants-1996_07
Patent number
US05541213

Reaction notes

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