Triethylamine → N-cyano-N'-(4-methylthiobenzyl)-4-pyridinecarboximidamide
Reaction equation
[C:1]([N:3]=[C:4]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)OC(C)C)#[N:2].Cl.[CH3:16][S:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.C(N(CC)CC)C>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)=[N:23][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([S:17][CH3:16])=[CH:19][CH:20]=1)#[N:2]Participants
5
Procedure
Isopropyl N-cyano-4-pyridinecarboximidate (0.40 g, 2.1 mmol) was dissolved in methanol (15 ml), and 4-methylthiobenzylamine hydrochloride (0.60 g, 3.2 mmol) and triethylamine (0.43 g, 4.2 mmol) were added. The mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was then concentrated under reduced pressure. The residual concentrate was extracted with ethyl acetate (50 ml×3). The ethyl acetate layer was washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual concentrate was crystallized from methanol-diethyl ether to give the title compound (0.29 g, 1.0 mmol, yield: 49%) as colorless crystals.
Workup
- concentrationthe reaction solution was then concentrated under reduced pressure
- concentrationThe residual concentrate
- extractionwas extracted with ethyl acetate (50 ml×3)
- washThe ethyl acetate layer was washed with water (100 ml)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- concentrationThe residual concentrate
- customwas crystallized from methanol-diethyl ether
Sources & evidence
- ORD record
- ord-5daa57fc6540410793f4c0b83f56f04c
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05272164
Reaction notes
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