Thionyl Chloride → HCID 13452204, compound

HRID 847749Notes

Reaction equation

HRID 847749 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20].S(Cl)([Cl:26])=O>C1C=CC=CC=1>[Cl:26][CH2:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 127800822-{3-[3-(Hydroxymethyl)phenoxy]propyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 13452204HCID 13452204, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.5 g of N-[3-[3-(hydroxymethyl)phenoxy]propyl]phthalimide was dissolved in 12 ml of benzene, and 3 ml of thionyl chloride was added. The mixture was refluxed for 1 hour. The solvent was distilled off under reduced pressure, and the residue was dissolved in ether. The solution was washed twice with a 5% aqueous solution of potassium carbonate, and then rinsed with water. The product was dried over anhydrous sodium sulfate, and the solvent was distilled off to afford 2.8 g of N-[3-[3-(chloromethyl)phenoxy]propyl]phthalimide as an oil.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in ether
  4. washThe solution was washed twice with a 5% aqueous solution of potassium carbonate
  5. washrinsed with water
  6. dry with materialThe product was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-4acc6f6d34994a98ae1d20f68d245aad
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

Loading…