Tetrahydrofuran → HCID 23508402, compound
Reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.O1CCCC1.Cl.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[N:34][CH:33]=1>O>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:17][CH:16]=2)[C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[N:34][CH:33]=2)=[CH:9][CH:10]=1)#[N:13]Participants
6
Procedure
224 mg of 4-[N-(4-hydroxybenzyl)amino]benzonitrile, 0.28 ml of triethylamine, and 7 ml of tetrahydrofuran were mixed, and 178 mg of nicotinoyl chloride hydrochloride was slowly added thereto, followed by stirring at room temperature overnight. After water was added to the reaction mixture, the product was extracted with tetrahydrofuran-diethyl ether (1:1). After the extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by TLC (using a 9:1 mixture of chloroform and acetone as the developing solvent) to obtain 292 mg of N-(4-cyanophenyl)-N-(4-hydroxybenzyl)-nicotinamide.
Workup
- extractionthe product was extracted with tetrahydrofuran-diethyl ether (1:1)
- washAfter the extract was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe resulting crude product was purified by TLC (
- additiona 9:1 mixture of chloroform and acetone as the developing solvent)
Sources & evidence
- ORD record
- ord-bae531d3710b4d55aa1a5e0668627c9f
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06762205B1
Reaction notes
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