Phthalimide → 2-{4-[(Oxan-2-yl)oxy]nonyl}-1H-isoindole-1,3(2H)-dione

HRID 1288342Notes

Reaction equation

HRID 1288342 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.Cl[CH2:13][CH2:14][CH2:15][CH:16]([O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CN(C)C=O>[O:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]1[O:22][CH:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14][CH2:13][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

4

Reactant 2

HCID 6809PhthalimideHCID 203276861-Chloro-4-(2-tetrahydropyranyloxy)nonane

Product 1

HCID 203276592-{4-[(Oxan-2-yl)oxy]nonyl}-1H-isoindole-1,3(2H)-dioneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

Sodium hydride (53%) (1.5 g. excess) is washed with benzene three times by decantation, then dimethyl formamide (100 ml.) is added. To this stirred suspension is added a solution of phthalimide (4.3 g., 0.03 mole) in dimethyl formamide (50 ml.) at such a rate as to keep the temperature below 35°C. A clear solution is obtained and to it is added 1-chloro-4-(2-tetrahydropyranyloxy)-nonane (7.8 g., 0.03 mole) and the resulting clear solution is stirred and heated at 95°C. for 20 hours. The reaction is then concentrated to one half its volume in vacuo, poured into ice water (200 ml.) and extracted with ether (2 × 150 ml.). The ether is washed with 5% sodium hydroxide (2 × 50 ml.), saturated sodium chloride solution (2 × 50 ml.) then dried over sodium sulfate. Evaporation of the ether affords 4.5 g. (45% yield) of N-[4-(2-tetrahydropyranyloxy)nonyl]phthalimide melting 59°- 61°C. After recrystallization from cyclohexane, the product melts at 62°-63°C.

Workup

  1. washSodium hydride (53%) (1.5 g. excess) is washed with benzene three times by decantation
  2. additiondimethyl formamide (100 ml.) is added
  3. customthe temperature below 35°C
  4. customA clear solution is obtained and to it
  5. concentrationThe reaction is then concentrated to one half its volume in vacuo
  6. additionpoured into ice water (200 ml.)
  7. extractionextracted with ether (2 × 150 ml.)
  8. washThe ether is washed with 5% sodium hydroxide (2 × 50 ml.), saturated sodium chloride solution (2 × 50 ml.)
  9. dry with materialthen dried over sodium sulfate
  10. customEvaporation of the ether
  11. customaffords 4.5 g

Sources & evidence

ORD record
ord-2903a0deb31b4a4db8be149dd1649212
Source dataset
uspto-grants-1976_10
Patent number
US03987091

Reaction notes

Loading…