Diethyl Ether → 2-(2,4-Difluorophenyl)-3-(2-cyanopyridin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

HRID 2380058Notes

Reaction equation

HRID 2380058 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([CH:16]([C:18]1[CH:23]=[CH:22][N+:21]([O-])=[CH:20][CH:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[CH3:26][N:27](C)C(Cl)=O.C[Si](C#N)(C)C.CCOCC>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([CH:16]([C:18]1[CH:23]=[CH:22][N:21]=[C:20]([C:26]#[N:27])[CH:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6598Dimethylcarbamoyl Chloride2×HCID 82115Trimethylsilyl cyanide2×HCID 18956544HCID 18956544, compound

Product 1

HCID 189565192-(2,4-Difluorophenyl)-3-(2-cyanopyridin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-olYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of part (i) (20.0 g) and N,N-dimethylcarbamoyl chloride (6.80 g) in dichloromethane (250 ml) was stirred at room temperature for 2.5 days, giving a clear solution. Trimethylsilyl cyanide (6.35 g) was added and stirring was continued for a further 48 hours. Additional quantities of N,N-dimethylcarbamoyl chloride (1.30 g) and trimethylsilyl cyanide (1.30 g) were then added and the solution was stirred for a further 36 hours. The reaction was then washed successively with 10% potassium carbonate solution, brine and then dried (MgSO4). Evaporation of the solvent gave a solid which was stirred with ether and filtered to give the title compound, (19.2 g), m.p. 188°-189°.

Workup

  1. customgiving a clear solution
  2. stirringstirring
  3. waitwas continued for a further 48 hours
  4. stirringthe solution was stirred for a further 36 hours
  5. washThe reaction was then washed successively with 10% potassium carbonate solution, brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent
  8. customgave a solid which
  9. filtrationfiltered

Sources & evidence

ORD record
ord-88eb80bdb13c4f9c912ccbd67baca23a
Source dataset
uspto-grants-1994_11
Patent number
US05364938

Reaction notes

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