Potassium Carbonate → HCID 53882417, compound

HRID 850052Notes

Reaction equation

HRID 850052 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Cl)[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C.O>[CH2:17]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 3424033-Hydroxybenzamide

Product 1

HCID 53882417HCID 53882417, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

3-hydroxybenzamide (0.5 g 3.6 mmol) was dissolved in dry acetonitrile (50 ml). To this was added potassium carbonate (0.503 g; 3.6 mmol) and cinnamyl chloride (0.5 ml; 3.6 mmol). This was left to reflux for 3.5 hours. The acetonitrile was removed under reduced pressure yielding a white sold which was dissolved in water (80 ml). The organics were extracted in dichloromethane (3×30 ml), dried over magnesium sulphate, filtered and the solvent removed under reduced pressure leaving a white solid. The solid was recrystallised from ethyl acetate and petrol (45%).

Workup

  1. waitThis was left
  2. temperatureto reflux for 3.5 hours
  3. customThe acetonitrile was removed under reduced pressure
  4. customyielding
  5. extractionThe organics were extracted in dichloromethane (3×30 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customleaving a white solid
  10. customThe solid was recrystallised from ethyl acetate and petrol (45%)

Sources & evidence

ORD record
ord-d33d5bd7772e4dc5af1b3b4c93c755de
Source dataset
uspto-grants-2000_01
Patent number
US06015827

Reaction notes

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