Cetyl Alcohol → HCID 19899498, compound

HRID 1030297Notes

Reaction equation

HRID 1030297 reaction equation
CS([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:8]=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:6]=1)(=O)=O.[CH2:23](O)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[CH2:38]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:8]=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:6]=1)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23]

Participants

6

Reactant 4

HCID 2682Cetyl AlcoholHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 12780501HCID 12780501, compound

Product 1

HCID 19899498HCID 19899498, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4'-Methanesulfonyl-2,2':6',2"-terpyridine (4.67 g, 0.015 mol) and hexadecyl alcohol (2,42 g, 0.010 mol) were added to N,N-dimethylformamide (0.1 liter). At 15° C., sodium hydride (60% content, oil dispersion, 0.8 g) was added thereto over a period of about 10 minutes. The entire solution was stirred for 30 minutes and then the reaction mixture was reacted under reflux for 4 hours. After cooling to room temperature, the reaction mixture was poured into an aqueous 4M sodium chloride solution (0.3 liter). The crystal that precipitated was taken out by filtration under suction and then washed with water and hexane. The crystal was again dissolved in chloroform and washed with 1M hydrochloric acid and water. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The resulting crystal was recrystallized from hexane to obtain 4.36 g of the above-entitled product (T-6). Yield: 92%. m.p. 97.5 to 99.0° C.

Workup

  1. customthe reaction mixture was reacted
  2. temperatureunder reflux for 4 hours
  3. customThe crystal that precipitated
  4. filtrationwas taken out by filtration under suction
  5. washwashed with water and hexane
  6. dissolutionThe crystal was again dissolved in chloroform
  7. washwashed with 1M hydrochloric acid and water
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe resulting crystal was recrystallized from hexane

Sources & evidence

ORD record
ord-c25b0536a0764eed9e23ede6179eb5fe
Source dataset
uspto-grants-1992_04
Patent number
US05104988

Reaction notes

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