Dimethylcarbamoyl Chloride → 2-(2,4-Difluorophenyl)-3-(6-cyanopyridin-2-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

HRID 1196945Notes

Reaction equation

HRID 1196945 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][CH:21]=[CH:20][N+:19]=1[O-])[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>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][CH:21]=[C:20]([C:26]#[N:27])[N:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 18956525HCID 18956525, compound

Product 1

HCID 189565382-(2,4-Difluorophenyl)-3-(6-cyanopyridin-2-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of part (i) (0.90 g), N,N-dimethylcarbamoyl chloride (0.80 g) and trimethylsilyl cyanide (0.80 g) in dichloromethane (10 ml) was stirred at room temperature for 7 days and the resulting solution was evaporated. The residue was treated with 5N hydrochloric acid (10 ml) and the mixture was agitated in an ultrasonic bath for 0.05 hour to give a clear solution. A solid formed on standing which was filtered off, washed with acetone followed by ether, and dried to give the title compound as the hydrochloride salt, (0.28 g), m.p. 219° (with decomposition).

Workup

  1. customthe resulting solution was evaporated
  2. additionThe residue was treated with 5N hydrochloric acid (10 ml)
  3. stirringthe mixture was agitated in an ultrasonic bath for 0.05 hour
  4. customto give a clear solution
  5. customA solid formed on standing which
  6. filtrationwas filtered off
  7. washwashed with acetone
  8. customdried

Sources & evidence

ORD record
ord-3bf86226591942d7aff0841870c76196
Source dataset
uspto-grants-1992_05
Patent number
US05116844

Reaction notes

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