N-Hydroxyphthalimide → Phthalimide

HRID 1755834Notes

Reaction equation

HRID 1755834 reaction equation
C(OC1C(=O)N=C(CO)NC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:38]1[C:42](=[O:43])[C:41]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:40]2[C:39]1=[O:48].N(C(OCC)=O)=NC(OCC)=O>CC(N(C)C)=O>[C:42]1(=[O:43])[NH:38][C:39](=[O:48])[C:40]2=[CH:47][CH:46]=[CH:45][CH:44]=[C:41]12

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178517848HCID 178517848, compound

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

5-(Benzyloxy)-2-(hydroxymethyl)-4(1H)-pyrimidinone (0.696 g) (3 mmol), 0.787 g (3 mmol) of triphenylphosphine and 0.489 g (3 mmol) of N-hydroxyphthalimide are dissolved in 50 ml of dimethylacetamide. A solution of 0.640 g (3.3 mmol) of diethyl azodicarboxylate in 2 ml of dimethylacetamide is added dropwise at 20° C. The mixture is stirred at room temperature for 20 hours, the solvent is evaporated in a high vacuum and the residual yellow oil is crystallized from ethanol/ether. After recrystallization from ethanol there is obtained N-[(5-benzyloxy)-1,4-dihydro-4-oxo-2-pyrimidinyl]methoxy]phthalimide as white crystals of m.p. 157° C.

Workup

  1. customthe solvent is evaporated in a high vacuum
  2. customthe residual yellow oil is crystallized from ethanol/ether
  3. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-bef5c801ed774d558a4abe532a07b99a
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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