Triethylamine → 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-[5-(N-methyl-carbamoylthio)-1,2,4-triazol-1-yl]-propan-2-ol

HRID 650645Notes

Reaction equation

HRID 650645 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[Cl:5][C:6]1([C:9]([OH:25])([CH2:18][N:19]2[C:23]([SH:24])=[N:22][CH:21]=[N:20]2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH2:8][CH2:7]1.C(N(CC)CC)C>O1CCCC1>[Cl:5][C:6]1([C:9]([OH:25])([CH2:18][N:19]2[C:23]([S:24][C:3](=[O:4])[NH:2][CH3:1])=[N:22][CH:21]=[N:20]2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 178520209HCID 178520209, compound

Product 1

HCID 217126512-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-[5-(N-methyl-carbamoylthio)-1,2,4-triazol-1-yl]-propan-2-olYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At room temperature, a solution of 0.3 ml (5 mmol) of methyl isocyanate in 5 ml of absolute tetrallydrofuran is added dropwise with stirring to a mixture of 1.72 g (5 mmol) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol, 0.1 ml of triethylamine and 20 ml of absolute tetrahydrofuran. After the addition, the reaction mixture is stirred at room temperature for 1 hour and then concentrated under reduced pressure. The crude product that remains is chromatographed over silica gel using a mixture of petroleum ether/ethyl acetate=1:1. Concentration of the eluate gives 1.3 g (65% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-[5-(N-methyl-carbamoylthio)-1,2,4-triazol-1-yl]-propan-2-ol in the form of an oil.

Workup

  1. additionAfter the addition
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product that remains is chromatographed over silica gel using
  4. additiona mixture of petroleum ether/ethyl acetate=1:1

Sources & evidence

ORD record
ord-da65f54e351f45db8bc6e6dea82b5772
Source dataset
uspto-grants-2001_08
Patent number
US06274610B1

Reaction notes

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