Methyl iodide → HCID 13505951, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[OH-].[Na+].[C:15](=[S:17])=[S:16].[CH3:18]I>CN(C)C=O.O>[NH:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:15](=[S:17])[S:16][CH3:18])=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:7]1=[O:12]Participants
Procedure
To a solution of 6-amino-3,4-dihydrocarbostyril (3.24 g) in dimethylformamide (10 ml) is added 20N aqueous sodium hydroxide (1.2 ml) with stirring at room temperature. To the mixture is further added carbon disulfide (1.57 ml), and the mixture is stirred at the same temperature for 1 hour. To the reaction mixture is added methyl iodide (1.56 ml) under ice-cooling, and the mixture is stirred at the same temperature for 2.5 hours. After the reaction, the reaction mixture is poured into water, and the resulting precipitate is separated by filtration, washed with water, purified by silica gel column chromatography (solvent; chloroform:methanol=100:1), and recrystallized from methanol twice to give methyl (3,4-dihydrocarbostyril-6-yl)-dithiocarbamate (2.0 g) as yellow needles, m.p. 203.5°-205.0° C.
Workup
- stirringthe mixture is stirred at the same temperature for 1 hour
- temperaturecooling
- stirringthe mixture is stirred at the same temperature for 2.5 hours
- customAfter the reaction
- customthe resulting precipitate is separated by filtration
- washwashed with water
- custompurified by silica gel column chromatography (solvent; chloroform:methanol=100:1)
- customrecrystallized from methanol twice
Sources & evidence
- ORD record
- ord-4622f196080149549d3a333f56f52abc
- Source dataset
- uspto-grants-1986_06
- Patent number
- US04593035
Reaction notes
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