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

HRID 851621Notes

Reaction equation

HRID 851621 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]1

Participants

4

Reactant 2

HCID 128556512-Bromo-1-(5-methyl-1,3-dioxan-5-yl)ethan-1-oneHCID 547199651,2,4-Triazolylsodium

Product 1

HCID 128556521-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-oneYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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, at 25° C., to a suspension, which is stirred under pure nitrogen, of 100.1 g (1.1 moles) of sodium 1,2,4-triazolide in 300 ml of dry tetrahydrofuran. After refluxing the mixture for eight hours, the inorganic precipitate is filtered off and the filtrate is concentrated to half its volume. The mixture is seeded and left to stand overnight at +3° C. The precipitate is filtered off, washed with 30 ml of cold tetrahydrofuran (at +5° C.), 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

  1. temperatureAfter refluxing the mixture for eight hours
  2. filtrationthe inorganic precipitate is filtered off
  3. concentrationthe filtrate is concentrated to half its volume
  4. waitleft
  5. filtrationThe precipitate is filtered off
  6. washwashed with 30 ml of cold tetrahydrofuran (at +5° C.)
  7. dry with materialwith 80 ml of ether and thereafter with 100 ml of n-pentane, and dried

Sources & evidence

ORD record
ord-c60dd0aadbc64e319974943f21535ec0
Source dataset
uspto-grants-1983_05
Patent number
US04385925

Reaction notes

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