1H-1,2,4-Triazole → HCID 13295576, compound

HRID 1032461Notes

Reaction equation

HRID 1032461 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.[I-].[CH3:19][S+](C)(C)=O.[OH-].[K+].[NH:26]1[CH:30]=[N:29][CH:28]=[N:27]1>C(O)(C)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([OH:15])([CH2:19][N:26]2[CH:30]=[N:29][CH:28]=[N:27]2)[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 14797Potassium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 13535401HCID 13535401, compound

Product 1

HCID 13295576HCID 13295576, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 1-(4-chlorophenoxy)3-(1,2,4-triazol-1-yl)propan-2-one (0.7g), trimethylsulphoxonium iodide (0.74g), potassium hydroxide (0.38g) and 1,2,4-triazole (0.23g) in tert butyl alcohol (15ml) was heated at 80° for 2.5h, then cooled and partitioned between ethyl acetate and water. The organic phase was separated, washed with water and then brine, dried and evaporated to dryness under reduced pressure. The residue was purified by chromatography on a Lobar silica column, using 2% methanol in chloroform as eluent, to give 2(4-chlorophenoxymethyl)1,3-di(1,2,4-triazol-1-yl)propan-2-ol as a gum. NMR in deuteriochloroform: δ 3.6(2H,s); 4.45(4H,q): 6.75(2H,d); 7.21(2H,d); 7.95(2H,s); 8.2(2H,s).

Workup

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialbrine, dried
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by chromatography on a Lobar silica column

Sources & evidence

ORD record
ord-8fdbd3b3fb6e4534a200bf093467f7e8
Source dataset
uspto-grants-1990_09
Patent number
US04957934

Reaction notes

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