Dimethylformamide → 3-Azido-1-methyl-4-phenylcarbostyril
Reaction equation
[N:1]([C:4]1[C:5](=[O:20])[NH:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N+:2]=[N-:3].[H-].[Na+].[CH3:23]N(C)C=O>>[N:1]([C:4]1[C:5](=[O:20])[N:6]([CH3:23])[C:7]2[C:12]([C:13]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N+:2]=[N-:3]Participants
Procedure
To a stirred suspension of 10.0 g of 3-azido-4-phenylcarbostyril in 125 ml. of dry dimethylformamide was added 2.2 g. of a 57 percent dispersion of sodium hydride in oil. After stirring at room temperature for about 45 minutes, the mixture was filtered to remove a small amount of insoluble material. To the clear solution was added 5 ml. of methyl iodide. The solution soon turned from an orange color to light yellow, accompanied by the formation of a precipitate. After 1 hour, the mixture was diluted with water and 10 g. (95 percent) of 3-azido-1-methyl-4-phenylcarbostyril, mp indefinite in the range of 140°-150° with decomposition, was collected. This material was pure by tlc. After recrystallizations from dimethylformamide-methanol, yellow needles were obtained, having a melting point of 140°-150° dec.
Workup
- filtrationthe mixture was filtered
- customto remove a small amount of insoluble material
- additionTo the clear solution was added 5 ml
- waitAfter 1 hour
- additionthe mixture was diluted with water and 10 g
- custom(95 percent) of 3-azido-1-methyl-4-phenylcarbostyril, mp indefinite in the range of 140°-150° with decomposition, was collected
- customAfter recrystallizations from dimethylformamide-methanol
- customyellow needles were obtained
Sources & evidence
- ORD record
- ord-9fb22f021add4edcb92ecd471a3277eb
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04014883
Reaction notes
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