N-Hydroxyphthalimide → N-[(4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxy]phthalimide

HRID 1755878Notes

Reaction equation

HRID 1755878 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:7][C:6]=2[C:5]([Cl:23])=[CH:4][C:3]=1[CH2:24][OH:25].O[N:27]1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[C:10]2[O:9][C:8]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:7][C:6]=2[C:5]([Cl:23])=[CH:4][C:3]=1[CH2:24][O:25][N:27]1[C:28](=[O:37])[C:29]2=[CH:36][CH:35]=[CH:34][CH:33]=[C:30]2[C:31]1=[O:32]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 199179894,7-Dichloro-2,2-diphenyl-1,3-benzodioxol-5-methanol

Product 1

HCID 19917897N-[(4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxy]phthalimideYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,7-Dichloro-2,2-diphenyl-1,3-benzodioxol-5-methanol (250 mg) (0.67 mmol), 108 mg (0.67 mmol) of N-hydroxyphthalimide and 175 mg (0.67 mmol) of triphenylphosphine are suspended in 20 ml of absolute tetrahydrofuran. 128 mg (0.73 mmol) of diethyl azodicarboxylate are added dropwise at 0° C. while stirring. The mixture is stirred at 0° C. for 1 hour and at room temperature for 24 hours. Subsequently, the solvent is removed in a high vacuum. The residue is crystallized and recrystallized from ethanol/diethyl ether. There are obtained 230 mg of N-[(4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxy]phthalimide as white crystals of m.p. 127°-129° C.

Workup

  1. stirringThe mixture is stirred at 0° C. for 1 hour and at room temperature for 24 hours
  2. customSubsequently, the solvent is removed in a high vacuum
  3. customThe residue is crystallized
  4. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-bd9d5feb09db4046ae72a32158be29b0
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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