Diethyl Ether → HCID 19978142, compound
Reaction equation
[ClH:1].[CH3:2][C:3]1[N:7]2[CH2:8][CH2:9][CH2:10][N:11]=[C:6]2[S:5][C:4]=1[C:12]([OH:14])=O.C(OCC)C>S(Cl)(Cl)=O>[ClH:1].[CH3:2][C:3]1[N:7]2[CH2:8][CH2:9][CH2:10][N:11]=[C:6]2[S:5][C:4]=1[C:12]([Cl:1])=[O:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In 75 ml of thionylchloride was suspended 10.0 g of 3-methyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carboxylic acid hydrochloride obtained in Example 27, followed by reflux under heating for 30 minutes. After dissolving completely, the reaction mixture was cooled. To the reaction mixture was added anhydrous diethylether under cooling with ice. The formed crystals were collected by filtration and dried over under reduced pressure to yield 10.7 g of 3-methyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonylchloridehydrochloride. In 5 ml of pyridine were dissolved 490 mg of this crystal and 0.2 ml of 3,5-dimethylaniline, followed by stirring at room temperature for 6 hours. The reaction mixture was concentrated and to the concentrate was added 5% sodium hydrogencarbonate aqueous solution. The precipitated crystals were collected by filtration and washed with diethylether. The resulting powder was suspended in diethylether. To the suspension was added 0.5 ml of saturated hydrogenchloride aqueous solution, followed by stirring at room temperature. The precipitated crystals were collected by filtration. The crystals were recrystallized from ethanol to obtain 216 mg of the titled compound.
Workup
- temperatureby reflux
- temperatureunder heating for 30 minutes
- dissolutionAfter dissolving completely
- temperaturethe reaction mixture was cooled
- temperatureunder cooling with ice
- filtrationThe formed crystals were collected by filtration
- customdried over under reduced pressure
Sources & evidence
- ORD record
- ord-e16e2f40f96549fea42915a53ebbdb41
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05599813
Reaction notes
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