Potassium Carbonate → HCID 19350310, compound

HRID 1636197Notes

Reaction equation

HRID 1636197 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16]([NH:19][CH2:20][CH:21]=[CH2:22])[CH:17]=[CH2:18]>CS(C)=O>[CH2:16]([N:19]([CH2:20][CH:21]=[CH2:22])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31279DiallylamineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 19350310HCID 19350310, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
157.5 °C

Procedure

Under an Ar atmosphere, 2.16 ml p-fluorobenzaldehyde and 3 ml DMSO were added sequentially to 3.5 g (30 mmol) of anhydrous K2CO3 , 3.70 ml (20 mmol) diallylamine. With constant stirring, the mixture was heated to about 155-160° C. After refluxing for 20 hours, the solution became intense red. The mixture was cooled to room temperature and 10 ml distilled water was added to dissolve any inorganic salts and the product was extracted with ether. The water layer was washed with ether several times and the combined organic layers were dried over MgSO4. The ether solution was then filtered and the ether, unreacted starting materials and solvent DMSO were removed by vacuum distillation at 100° C. A very viscous orange red product was left in the flask. Yield=2.05 g (51%). Mass spectrum: M+ /e=201. Calcd. M+ /e=201.27 Anal. calcd. for C13H15NO, C, 77.58; H, 7.51; N, 6.96. Found: C, 77.33; H, 7.33; N, 6.66. 1H NMR(CDCl3), δ 9.71 (1H,s), 7.70 (2H, d, J=9Hz), 6.70 (2H, d, J=9Hz), 5.82 (2H, m), 5.19 (4H, m), 4.00 (4H,t). 13C NMR (CDCl3) δ 189.4, 152.8, 131.8, 116.8, 110.9, 52.22 ppm.

Workup

  1. temperatureAfter refluxing for 20 hours
  2. temperatureThe mixture was cooled to room temperature
  3. distillation10 ml distilled water
  4. additionwas added
  5. dissolutionto dissolve any inorganic salts
  6. extractionthe product was extracted with ether
  7. washThe water layer was washed with ether several times
  8. dry with materialthe combined organic layers were dried over MgSO4
  9. filtrationThe ether solution was then filtered
  10. customwere removed by vacuum distillation at 100° C
  11. waitA very viscous orange red product was left in the flask

Sources & evidence

ORD record
ord-de83404e40914423a01ddc2763edc3e7
Source dataset
uspto-grants-2000_03
Patent number
US06033774

Reaction notes

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