Pyridine → HCID 54501726, compound
Reaction equation
[N:1]1[CH:6]=CC=C[CH:2]=1.Cl.C([C:11]1[N:15]2[CH2:16][CH2:17][CH2:18][N:19]=[C:14]2SC=1C(Cl)=O)CC.C(SC1C=CC(N)=CC=1)CCCCCC>CN(C)C=O>[CH3:11][NH:15][C:16]1[CH:2]=[N:1][CH:6]=[C:18]([NH:19][CH3:14])[CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In the mixture of 50 ml of pyridine and 5 ml of dimethylformamide was suspended 1.07 g of 3-propyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonylchloride hydrochloride (described in Example 13). To the suspension were added 850 mg of 4-n-heptylthioaniline obtained in Reference Example 6, and 56 mg of 3,5-dimethylaminopyridine, followed by stirring at 70° C. for 12 hours. The reaction mixture was concentrated and to the concentrate was added saturated sodium hydrogencarbonate aqueous solution. The mixture was extracted with chloroform. The extract was washed with saturated sodium chloride aqueous solution, dried over anhydrous potassium carbonate and treated with active carbon. The solvent was removed under reduced pressure. The residue was dissolved in ethanol. To the mixture was added saturated hydrogenchloride diethylether solution, followed by stirring at room temperature. The solvent was removed under reduced pressure. The residue was precipitated from ethanol-diethylether to collect by filtration. The precipitated powder was recrystallized from methanoldiethylether to yield 992 mg of the titled compound.
Sources & evidence
- ORD record
- ord-702f7ef0cf51474b951af0e9aa563034
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05599813
Reaction notes
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