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Potassium Carbonate → 2-(2,4-Dichlorophenyl)-1-(1,2,4-triazol-1-yl)-3-(5-trifluoromethylimidazol-1-yl)-propan-2-ol

HRID 1583761
Notes
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Reaction equation

HRID 1583761 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[N:4]=[CH:5][NH:6][CH:7]=1.S(O)(=O)(=O)C.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[C:23]1([CH2:26][N:27]2[CH:31]=[N:30][CH:29]=[N:28]2)[CH2:25][O:24]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[C:23]([OH:24])([CH2:25][N:4]1[C:3]([C:2]([F:9])([F:8])[F:1])=[CH:7][N:6]=[CH:5]1)[CH2:26][N:27]1[CH:31]=[N:30][CH:29]=[N:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 867396002-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane methanesulphonateHCID 178418921HCID 178418921, compound

Product 1

HCID 202583642-(2,4-Dichlorophenyl)-1-(1,2,4-triazol-1-yl)-3-(5-trifluoromethylimidazol-1-yl)-propan-2-olYield 1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 4-trifluoromethylimidazole (0.7 g, 5 mmole), 2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-oxirane mesylate salt (1.88 g, 5 mmole) and anhydrous potassium carbonate (2.0 g, 14 mmole) in dry N,N-dimethylformamide (20 ml) was heated at 75°-80° C. for 18 hours. The solvent was evaporated under vacuum and the residue was partitioned between water (20 ml) and methylene chloride (50 ml). The aqueous layer was separated and extracted twice with methylene chloride (30 ml). The organic layers were combined, dried over magnesium sulphate and evaporated to yield the crude product containing the 4- and 5-trifluoromethyl-imidazolyl isomers. The residue was chromatographed on silica eluting with a mixture of hexane, isopropyl alcohol and concentrated ammonium hydroxide (80:20:1.5); fractions containing the minor component were evaporated and the product recrystallised from a mixture of acetone and water to give the desired title compound (0.02 g, 1%), m.p. 190°-192° C.

Workup

  1. temperaturewas heated at 75°-80° C. for 18 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe residue was partitioned between water (20 ml) and methylene chloride (50 ml)
  4. customThe aqueous layer was separated
  5. extractionextracted twice with methylene chloride (30 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customto yield the crude product
  9. customThe residue was chromatographed on silica eluting with a mixture of hexane, isopropyl alcohol and concentrated ammonium hydroxide (80:20:1.5)
  10. additionfractions containing the minor component
  11. customwere evaporated
  12. customthe product recrystallised from a mixture of acetone and water

Sources & evidence

ORD record
ord-111e71b6ea584342a2b1fd4b45b44227
Source dataset
uspto-grants-1985_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04554286

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes