Acetic Acid → 1-Chloro-2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)-2-(trimethylsilyloxy) propane

HRID 725773

Reaction equation

HRID 725773 reaction equation
[O:1]1[C:3]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[F:13])([CH2:4][Cl:5])[CH2:2]1.[CH3:14][Si:15]([CH3:22])([CH3:21])N1C=NC=N1.[N:23]1([K])[CH:27]=[N:26][CH:25]=[N:24]1.C(O)(=O)C>CN(C)C=O.O>[Cl:5][CH2:4][C:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])([O:1][Si:15]([CH3:22])([CH3:21])[CH3:14])[CH2:2][N:23]1[CH:27]=[N:26][CH:25]=[N:24]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 875581-Trimethylsilyl-1,2,4-triazoleHCID 111833262-(Chloromethyl)-2-(2,4-difluorophenyl)oxiraneHCID 178506625HCID 178506625, compound

Product 1

HCID 155169021-Chloro-2-(2,4-difluorophenyl)-3-(1,2,4-triazol-1-yl)-2-(trimethylsilyloxy) propane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4.11 g (0.02 moles) of 1,2-epoxy-2-(2,4-difluorophenyl)-3-chloropropane are reacted with 4.23 g (0.03 moles) of 1-(trimethylsilyl)-1,2,4-triazole and 0.1 g (0.001 mole) of 1,2,4-triazol-1-yl potassium in 50 ml of dimethyl formamide at 50° C. for 2 hours. Then the reaction mixture is neutralized by glacial acetic acid, mixed with 250 ml of water at room temperature and extracted twice with 50 ml of dichloromethane each. The combined extracts are washed three times with 50 ml of water each, dried over water-free sodium sulfate and evaporated in vacuo. The residue is subjected to column chromatography by the method of Example 4 above. After crystallization from n-heptane 4.9 g (71.5%) of the title compound are obtained; m.p.: 59°-61° C.

Workup

  1. extractionextracted twice with 50 ml of dichloromethane each
  2. washThe combined extracts are washed three times with 50 ml of water each,
  3. dry with materialdried over water-free sodium sulfate
  4. customevaporated in vacuo
  5. customAfter crystallization from n-heptane 4.9 g (71.5%) of the title compound
  6. customare obtained

Sources & evidence

ORD record
ord-367257a8e929448c9b0a58c5707eb0e8
Source dataset
uspto-grants-1998_01
Patent number
US05707976

Linked notes

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