Potassium Carbonate → HCID 23001290, compound

HRID 844264Notes

Reaction equation

HRID 844264 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.Br[CH2:11][CH2:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3[C:16](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]2=[O:24])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 849893-Methoxybenzenethiol

Product 1

HCID 23001290HCID 23001290, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-methoxybenzenethiol (1.52 mL, 12.2 mmol), N-(3-bromopropyl)phthalimide (3.28 g, 12.2 mmol), and potassium carbonate (2.53 g, 18.3 mmol) in acetone (50 mL) was heated to reflux for 88 hours. The solvent was removed in vacuo and the residue partitioned between water (50 mL) and methylene chloride (50 mL). The layers were separated and the aqueous layer washed with methylene chloride (2×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a yellow oil. The crude product was purified by column chromatography (0→50% ethyl acetate/hexane) to provide the title compound as a clear oil.

Workup

  1. temperatureto reflux for 88 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between water (50 mL) and methylene chloride (50 mL)
  4. customThe layers were separated
  5. washthe aqueous layer washed with methylene chloride (2×50 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto provide a yellow oil
  10. customThe crude product was purified by column chromatography (0→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fe6971f75e7242eeb1238b4dc019b9ca
Source dataset
uspto-grants-2002_04
Patent number
US06380228B1

Reaction notes

Loading…