Phthalimide → N-(3-nitrophenethyl)phthalimide

HRID 1005680Notes

Reaction equation

HRID 1005680 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8]O)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][N:36]1[C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]2[C:32]1=[O:42])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 1040583-Nitrophenylethyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 22674056N-(3-nitrophenethyl)phthalimide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (225 ml) was dissolved 15 g of 3-nitrophenethyl alcohol, followed by adding triphenylphosphine (26 g) and phthalimide (13.9 g). Then, the resulting mixture was ice-cooled, followed by dropwise addition of diethyl azodicarboxylate (15.5 ml). After stirring at room temperature for 1 hour, the resulting crystals were collected by filtration, washed with diethyl ether and dried, to give N-(3-nitrophenethyl)phthalimide as colorless crystals.

Workup

  1. temperaturecooled
  2. filtrationthe resulting crystals were collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-ecef675d63c44e868d896515a77f310c
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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