Reaction equation
C(O[C:4](=[O:16])[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)C.[C:17]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)#[N:18].CC(C)([O-])C.[K+].[CH3:31][S:32]N=C=O.IC.[CH3:38][N:39]([CH3:42])C=O>>[CH3:38][N:39]1[C:4](=[O:16])[C:5]([C:6]2[CH:15]=[CH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=2)=[C:17]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[N:18]=[C:42]1[S:32][CH3:31]Participants
Procedure
To a stirring solution of ethyl-2-naphthylacetate (10.0 g, 46.7 mmol) and 4-cyanopyridine (4.86 g, 46.7 mmol) in 50 mL dry dimethylformamide (DMF) at room temperature under nitrogen was added 47 mL potassium tert-butoxide (1.0 M in 2-methyl-2-propanol) dropwise via syringe. The dark red solution was stirred at room temperature for 75 min. Methylthioisocyanate (3.41 g, 46.7 mmol) in 10 mL DMF added whole. The solution was stirred for 90 min at room temperature. Iodomethane (2.95 mL, 46.7 mmol) was added dropwise over a 3 min period. Solid precipitates out of reaction. Continued to stir as a mixture for 30 min. Water (500 mL) was slowly added to reaction mixture. The solid was collected via filtration then washed with water, cold ethanol (50 mL), and ether. The solid was air dried for 3 days. M+1=360.2.
Workup
- stirringThe solution was stirred for 90 min at room temperature
- customSolid precipitates out of reaction
- stirringto stir as a mixture for 30 min
- additionWater (500 mL) was slowly added to reaction mixture
- filtrationThe solid was collected via filtration
- washthen washed with water, cold ethanol (50 mL), and ether
- customdried for 3 days
Sources & evidence
- ORD record
- ord-77270c2e721440a28b95e897fee0bb01
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429594B2
Linked notes
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