Cetyl Alcohol → HCID 19864557, compound

HRID 1200043Notes

Reaction equation

HRID 1200043 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)=[N:8][CH:9]=1)([OH:3])=[O:2].[CH2:15](O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>S(Cl)(Cl)=O.N1C=CC=CC=1>[NH:14]1[CH:13]=[CH:12][N:11]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([C:1]([O:3][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])=[O:2])=[CH:9][N:8]=1

Participants

5

Reactant 2

HCID 2682Cetyl AlcoholHCID 19864555HCID 19864555, compound

Product 1

HCID 19864557HCID 19864557, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24386Thionyl ChlorideSolvent

Procedure

5-Carboxy-2-(2-imidazolyl)-pyridine (1.89 g, 0.01 mol) is refluxed in 10 ml of thionyl chloride for 2 h. The solution is evaporated to dryness and the residue dissolved in 20 ml of dichloromethane. The latter solution is added dropwise to a mixture of 1-hexadecanol (2.68 g, 0.011 mol) in 1.6 ml of pyridine. After 17 h at room temperature, the precipitate is filtered off and the filtrate evaporated to dryness. The resulting residue is crystallized in toluene to yield the title compound, m.p. 97°-98°.

Workup

  1. customThe solution is evaporated to dryness
  2. dissolutionthe residue dissolved in 20 ml of dichloromethane
  3. filtrationthe precipitate is filtered off
  4. customthe filtrate evaporated to dryness
  5. customThe resulting residue is crystallized in toluene

Sources & evidence

ORD record
ord-452e13af0aa84608bbcb086dff599332
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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