Pyridine → 4-(4-(Octadecanoylamino)butyl)-1,10-phenanthroline
Reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].S(Cl)(Cl)=O.N1C=CC=CC=1.[NH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]1[C:49]2[C:40](=[C:41]3[C:46](=[CH:47][CH:48]=2)[CH:45]=[CH:44][CH:43]=[N:42]3)[N:39]=[CH:38][CH:37]=1>O>[C:1]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]1[C:49]2[C:40](=[C:41]3[C:46](=[CH:47][CH:48]=2)[CH:45]=[CH:44][CH:43]=[N:42]3)[N:39]=[CH:38][CH:37]=1)(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of octadecanoic acid (170 mg, 0.6 mmol) and thionyl chloride (4 mL) was heated at 60° C. for 1 hour. The mixture was then cooled to room temperature, whereupon it was concentrated in vacuo. Residue from this mixture was then dissolved in CH2Cl2 (10 mL), whereupon pyridine (5 equivalents) and 4-(aminobutyl)-1,10-phenanthroline (1 equivalent) (Wang et al., Adv. Funct. Mater., 12, 415-419 (2002)) were added. The resulting mixture was stirred at room temperature overnight and then poured into H2O. The resulting precipitate was collected by suction filtration and dried to a constant weight to give 4-(4-(octadecanoylamino)butyl)-1,10-phenanthroline.
Workup
- temperatureThe mixture was then cooled to room temperature, whereupon it
- concentrationwas concentrated in vacuo
- dissolutionResidue from this mixture was then dissolved in CH2Cl2 (10 mL)
- filtrationThe resulting precipitate was collected by suction filtration
- customdried to a constant weight
Sources & evidence
- ORD record
- ord-2ddcdda86a494547a086f4a5328a379c
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193746B2
Reaction notes
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