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1H-1,2,4-Triazole → HCID 14403430, compound

HRID 1650733
Notes
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Reaction equation

HRID 1650733 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][C:11]1([C:14]2([S:17][CH2:18][CH2:19][CH3:20])[CH2:16][CH2:15]2)[CH2:13][O:12]1.[NH:21]1[CH:25]=[N:24][CH:23]=[N:22]1.CC(C)([O-])C.[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([C:14]1([S:17][CH2:18][CH2:19][CH3:20])[CH2:16][CH2:15]1)([OH:12])[CH2:13][N:21]1[CH:25]=[N:24][CH:23]=[N:22]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 23665647Potassium tert-butoxideHCID 540874812-(2,4-Dichlorophenylethenyl)-2-(1-propylmercaptocyclopropyl) oxirane

Product 1

HCID 14403430HCID 14403430, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 38.2 g (0.12 mol) of 2-(2,4-dichlorophenylethenyl)-2-(1-propylmercaptocyclopropyl) oxirane in 30 ml of dimethylformamide is added dropwise under a nitrogen atmosphere and with stirring at 80° C. to a mixture of 24 g (0.35 mol) of 1,2,4-triazole, 2.7 g (0.02 mol) of potassium tert.-butoxide and 50 ml of dimethylformamide. The mixture is stirred at 80° C. for 6 hours, then the solvent is removed under reduced pressure, and the residue is taken up in ethyl acetate/toluene, washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue which remains is chromatographed on silica gel using chloroform as the eluant. In this manner, 12.1 g (26% of theory) of trans-4-(2,4-dichlorophenyl)-2-(1-propylmercaptocyclopropyl)1-(1,2,4-triazol-1-yl)-but-3-en-2-ol are obtained in the form of an oily product.

Workup

  1. customthe solvent is removed under reduced pressure
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue which remains is chromatographed on silica gel

Sources & evidence

ORD record
ord-ba115882bbec43588ffe3edd859fcbaa
Source dataset
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04925865

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes