1-(Diphenylmethyl)azetidin-3-yl methanesulfonate → 2-[1-(diphenylmethyl)azetidin-3-yl]-1H-isoindole-1,3(2H)-dione

HRID 1766189Notes

Reaction equation

HRID 1766189 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K]>CN(C)C=O>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10]([N:27]3[C:26](=[O:28])[C:25]4=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]4[C:23]3=[O:33])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 134919172-[1-(diphenylmethyl)azetidin-3-yl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 75 g (0.235 mol) of 1-(diphenylmethyl)-3-(methanesulphonyloxy)-azetidine, 47.1 g (0.254 mol) of potassium phthalimide and 800 ml of dimethylformamide was refluxed for 1½ hours, during which time a fine precipitate gradually settled out. After cooling the precipitate was filtered off and the solvent was evaporated off in vacuo, finally under a high vacuum. The colourless residue crystallised when left to stand. Yield: 78.0 g (90% of theoretical). Rf=0.95 (El N).

Workup

  1. temperaturewas refluxed for 1½ hours, during which time a fine precipitate
  2. temperatureAfter cooling the precipitate
  3. filtrationwas filtered off
  4. customthe solvent was evaporated off in vacuo, finally under a high vacuum
  5. customThe colourless residue crystallised when
  6. waitleft

Sources & evidence

ORD record
ord-ecda97ac29bf4f388126e48ab8841617
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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