1-Bromo-3-chloropropane → 5-(5-[(3-chloropropyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl)-2-methylquinoline
Reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13]([CH3:19])=[N:14]3)=[N:7][NH:6][C:5]1=[S:20].Br[CH2:22][CH2:23][CH2:24][Cl:25]>>[Cl:25][CH2:24][CH2:23][CH2:22][S:20][C:5]1[N:4]([CH3:3])[C:8]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13]([CH3:19])=[N:14]3)=[N:7][N:6]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydride (2.65 g, 60% in oil) was added portionwise to stirred absolute ethanole at 0° C., under a nitrogen atmosphere. Then 4-methyl-5-(2-methyl-5-quinolinyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (21.8 g) (intermediate 7) was added portionwise and the reaction mixture was allowed to reach room temperature. Then 1-bromo-3-chloropropane (12.6 ml) was added over 10 min and the reaction mixture was brought to 80° C. and left to react an additional hour after which time the reaction mixture was allowed to reach room temperature and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel with 90% ethyl acetate-acetone to give the title compound (14.18 g) as a white solid.
Workup
- customto reach room temperature
- customwas brought to 80° C.
- waitleft
- customto react an additional hour after which time the reaction mixture
- customto reach room temperature
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by chromatography on silica gel with 90% ethyl acetate-acetone
Sources & evidence
- ORD record
- ord-e3ae5cd3a7994d0ebb83e514b66646e4
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003638B2
Reaction notes
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