Phthalimide → HCID 11069145, compound

HRID 2280239Notes

Reaction equation

HRID 2280239 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[CH3:31][N:32]1[C:37]([CH3:38])=[CH:36][C:35](=[O:39])[C:34]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:33]1[CH2:48]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:31][N:32]1[C:37]([CH3:38])=[CH:36][C:35](=[O:39])[C:34]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:33]1[CH2:48][N:24]1[C:20](=[O:30])[C:21]2=[CH:29][CH:28]=[CH:27][CH:26]=[C:22]2[C:23]1=[O:25]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11807400HCID 11807400, compound

Product 1

HCID 11069145HCID 11069145, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.6 g triphenylphosphine (32 mmol, 1.2 equiv) and 4.8 g phthalimide (32 mmol, 1.2 equiv) were added to a stirred suspension of 58 (7 g, 27 mmol, 1 equiv) in 150 ml THF at 0° C. 6.47 g Diisopropyl azodicarboxylate [DIAD] (32 mmol, 1.2 equiv) was added dropwise over 30 minutes. The solution was allowed to warm to room temperature and was stirred for a further 17 hours, after which time the solution was filtered. The solid was washed with cold THF to give 9.92 g of a white amorphous solid in 95% yield.

Workup

  1. filtrationafter which time the solution was filtered
  2. washThe solid was washed with cold THF

Sources & evidence

ORD record
ord-cdb8ef43e8df4ad5bc7e3bbe703b8493
Source dataset
uspto-grants-2015_09
Patent number
US09138495B2

Reaction notes

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