2-Bromo-1-(5-methyl-1,3-dioxan-5-yl)ethan-1-one → 1-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one
Reaction equation
[CH3:1][C:2]1([C:8](=[O:11])[CH2:9]Br)[CH2:7][O:6][CH2:5][O:4][CH2:3]1.[NH:12]1[CH:16]=[N:15][C-:14]=[N:13]1.[Na+]>O1CCCC1>[CH3:1][C:2]1([C:8](=[O:11])[CH2:9][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1Participants
Procedure
A solution of 223 g (1 mole) of 1-(5-methyl-1,3-dioxan-5-yl)-2-bromoethan-1-one in 200 ml of tetrahydrofuran is added dropwise in the course of 2 hours to a suspension, stirred under pure nitrogen, of 100 g (1.1 moles) of sodium 1,2,4-triazolide in 300 ml of dry tetrahydrofuran, at 25° C. The mixture is refluxed for 8 hours, the inorganic precipitate is then filtered off, and the filtrate is concentrated to half its volume. It is then seeded and left to stand overnight at +3° C. The precipitate is filtered off, washed with 30 ml of cold (+5° C.) tetrahydrofuran, then with 80 ml of ether and thereafter with 100 ml of n-pentane, and dried. 184 g (87.2%) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one are obtained as white crystals of melting point 95°-97° C.
Workup
- temperatureThe mixture is refluxed for 8 hours
- filtrationthe inorganic precipitate is then filtered off
- concentrationthe filtrate is concentrated to half its volume
- waitleft
- filtrationThe precipitate is filtered off
- washwashed with 30 ml of cold (+5° C.) tetrahydrofuran
- dry with materialwith 80 ml of ether and thereafter with 100 ml of n-pentane, and dried
Sources & evidence
- ORD record
- ord-85eed79ad7b74efe932401097ff4ae63
- Source dataset
- uspto-grants-1983_01
- Patent number
- US04368066
Reaction notes
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