3-Pyridinecarbonyl chloride, hydrochloride (1:1) → (3-Pyridinyl) (1,2,3,4-tetrahydro-2-thioxo-6-quinazolinyl)methanone
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][NH:7][C:6]1=[S:15].Cl.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23](Cl)=[O:24])[CH:18]=1>CN(C)C=O>[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[NH:5][C:6](=[S:15])[NH:7][CH2:8]3)=[O:24])[CH:18]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
106 Parts of N,N-dimethylformamide were added dropwise to 650 parts of aluminum chloride and the solution was stirred for 15 min at 75° C. There were added portionwise 112 parts of 3,4-dihydro-2(1H)-quinazolinethione and, after stirring for 15 min at 75° C., 136 parts of 3-pyridinylcarbonyl chloride hydrochloride. Stirring at 75° C. was continued overnight and then the mixture was poured into 2500 parts of ice-water. The precipitate was filtered off and stirred for 13 hours in a mixture of ice-water and 1530 parts of a sodium hydroxide solution 50%. The product was filtered off, washed with water and dried, yielding 150 parts (82%) of (3-pyridinyl) (1,2,3,4-tetrahydro-2-thioxo-6-quinazolinyl)methanone; (decomp.) (interm. 54).
Workup
- stirringafter stirring for 15 min at 75° C.
- stirringStirring at 75° C.
- waitwas continued overnight
- filtrationThe precipitate was filtered off
- stirringstirred for 13 hours in a mixture of ice-water and 1530 parts of a sodium hydroxide solution 50%
- filtrationThe product was filtered off
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-3c5e66dfaabe4ada822bf008a916ad1b
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05120845
Reaction notes
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