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

HRID 1004667Notes

Reaction equation

HRID 1004667 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 8028TetrahydrofuranSolvent2×

Procedure

At room temperature, a solution of 0.3 ml (5 mmol) of methyl isocyanate in 5 ml of absolute tetrahydrofuran 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-(l -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-6c9c031b097c446dbd10e7f3d958fbd8
Source dataset
uspto-grants-2000_04
Patent number
US06051592

Reaction notes

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