Phthalimide → Phthalimide, N-(3-methyl-2-butenyl)-

HRID 1779741Notes

Reaction equation

HRID 1779741 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17].C(OCC)(=O)C.CCCCCC>CN(C=O)C>[CH3:17][C:16]([CH3:18])=[CH:15][CH2:14][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 700922-Butene, 1-bromo-3-methyl-HCID 5462222PotassiumHCID 21226206Ethyl acetate hexane

Product 1

HCID 96648Phthalimide, N-(3-methyl-2-butenyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phthalimide, potassium salt (20.5 g, 0.11 mol) was suspended in dry DMF (100 mL). To the suspension was added 1-bromo-3-methyl-2-butene (14.8 g, 0.1 mol) with stirring. The reaction mixture was stirred under N2 at 45° C. for 24 h. TLC (silica gel, 30% ethyl acetate-hexane) showed one major UV-visible spot with Rf =0.65. DMF was removed under vacuum and the residue was taken up with water (200 mL) and extracted with ethyl acetate (3×150 mL). The extracts were combined and dried over Na2SO4. Evaporation of solvent gave the title product as a white solid. Yield: 21.0 g (98%). mp: 95°-97° C. MS: 233 (M+NH4)+, 216 (M+H)+. 1H NMR (CDCl3) ε 1.71 and 1.83 [s, 6H, C(CH3)2 ], 4.26 (d, J=6.6 Hz, 2H, CH2CH=), 5.30 (t, 1H, CH=), 7.67 to 7.86 (m, 4H, Aromatic-H).

Workup

  1. stirringThe reaction mixture was stirred under N2 at 45° C. for 24 h
  2. customDMF was removed under vacuum
  3. extractionextracted with ethyl acetate (3×150 mL)
  4. dry with materialdried over Na2SO4
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-78a5c5c55ecf4a63b43c061ec28d9362
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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