1H-1,2,4-Triazole → 1-(1H-1,2,4-triazol-1-yl)-2-isopropoxy-2-(2,4-dichlorophenyl)pentane

HRID 2166416Notes

Reaction equation

HRID 2166416 reaction equation
N(C(OC)=O)=NC(OC)=O.[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19]([O:25][CH:26]([CH3:28])[CH3:27])([CH2:22][CH2:23][CH3:24])[CH2:20]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:48]1[CH:52]=[N:51][CH:50]=[N:49]1>O1CCCC1>[N:48]1([CH2:20][C:19]([O:25][CH:26]([CH3:28])[CH3:27])([C:13]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=2[Cl:11])[CH2:22][CH2:23][CH3:24])[CH:52]=[N:51][CH:50]=[N:49]1

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 230397132-(2,4-Dichlorophenyl)-2-isopropoxypentan-1-ol

Product 1

HCID 230396861-(1H-1,2,4-triazol-1-yl)-2-isopropoxy-2-(2,4-dichlorophenyl)pentane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.5 g (30 mmoles) of dimethyl azodicarboxylate is added dropwise, at room temperature, to a solution of 5.8 g (20 mmoles) of 2-(2,4-dichlorophenyl)-2-isopropoxypentan-1-ol, 7.9 g (30 mmoles) of triphenylphosphine and 1.66 g (24 mmoles) of 1,2,4-triazole in 100 ml of absolute tetrahydrofuran, and the reaction mixture is then stirred for 3 hours at room temperature and then for a further 16 hours at 50° C. and is evaporated; the residue is digested with 100 ml of diethyl ether, the insoluble residue is filtered off, and the ether phase is concentrated again and purified by column chromatography (silica gel; 1:1 ethyl acetate/petroleum ether). This gives a colourless oil having physical data which agree entirely with those in Example 3b).

Workup

  1. waitfor a further 16 hours at 50° C.
  2. customis evaporated
  3. filtrationthe insoluble residue is filtered off
  4. concentrationthe ether phase is concentrated again
  5. custompurified by column chromatography (silica gel; 1:1 ethyl acetate/petroleum ether)
  6. customThis gives a colourless oil

Sources & evidence

ORD record
ord-a1dba695f8394a7299a3bd7fff9ac90f
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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