Dimethylformamide → HCID 13605070, compound
Reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7](=NO)[CH3:8])=[CH:4][CH:3]=1.[ClH:11].[NH2:12]O.P(Cl)(Cl)(Cl)=O.[CH3:19][N:20]([CH3:23])C=O>O.CCOCC>[CH3:1][C:2]1[S:6][C:19]2=[N:20][C:23]([Cl:11])=[C:7]([C:8]#[N:12])[CH:5]=[C:4]2[CH:3]=1Participants
Conditions
- Temperature
- 10 °C
Procedure
A suspension was prepared from 25 g of 5-methyl-2-acetylthiophene oxime (obtained by reacting the appropriate ketone with hydroxylamine hydrochloride by standard procedures) and 250 ml of ether and this was cooled to 10° C. in an ice bath. Phosphoryl chloride (80 ml) was then added to the stirred suspension over a period of 15 minutes. The mixture was then allowed to warm to room temperature over a period of 16 hours. Then, 21 g of dimethylformamide was added over 10 minutes and the mixture was heated to 110° C. to boil off the ether. Heating was continued at 110° C. for 3.5 hours and then 11.2 g of hydroxylamine hydrochloride was added in portions over 20 minutes. The mixture was cooled and poured into 700 ml of water and the precipitate which formed was collected by filtration. This was recrystallized from acetone to give 2-methyl-6-chlorothieno[2,3-b]pyridine-5-carbonitrile melting at about 171°-173° C.
Workup
- customobtained
- temperatureto warm to room temperature over a period of 16 hours
- temperaturethe mixture was heated to 110° C.
- temperatureHeating
- temperatureThe mixture was cooled
- customthe precipitate which formed
- filtrationwas collected by filtration
- customThis was recrystallized from acetone
Sources & evidence
- ORD record
- ord-24b075938ed6410eb07d25576da3b602
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04581448
Reaction notes
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