Methyl chloroformate → 2-(1-Chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-methoxycarbonylthio-1,2,4-triazol-1-yl)-propan-2-ol

HRID 650644Notes

Reaction equation

HRID 650644 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].C(N(CC)CC)C.[Cl:13][C:14]1([C:17]([OH:33])([CH2:26][N:27]2[C:31]([SH:32])=[N:30][CH:29]=[N:28]2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[CH2:16][CH2:15]1>ClCCl>[Cl:13][C:14]1([C:17]([OH:33])([CH2:26][N:27]2[C:31]([S:32][C:2]([O:4][CH3:5])=[O:3])=[N:30][CH:29]=[N:28]2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178520209HCID 178520209, compound

Product 1

HCID 217126482-(1-Chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-methoxycarbonylthio-1,2,4-triazol-1-yl)-propan-2-olYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

At temperatures between 0 and 5° C., first a solution of 1.28 ml (6 mmol) of methyl chloroformate in 10 ml of absolute dichloromethane and then 0.84 ml (6 mmol) of triethylamine are 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 and 10 ml of absolute dichloromethane. After the addition, the reaction mixture is stirred at room temperature for a further 2 hours and then diluted with dichloromethane and washed with ice-cold aqueous sodium carbonate solution. The organic phase is dried over sodium sulphate and subsequently concentrated under reduced pressure. The 1.7 g of crude product that remain are chromatographed over silica gel using a mixture of petroleum ether/ethyl acetate=1:1. Concentration of the eluate gives 0.7 g (35% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-methoxycarbonylthio-1,2,4-triazol-1-yl)-propan-2-ol in the form of an oil.

Workup

  1. additionAfter the addition
  2. washwashed with ice-cold aqueous sodium carbonate solution
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationsubsequently concentrated under reduced pressure
  5. customThe 1.7 g of crude product that remain are chromatographed over silica gel using
  6. additiona mixture of petroleum ether/ethyl acetate=1:1

Sources & evidence

ORD record
ord-cf9da1e2626b4dddac9379c1f0c3b673
Source dataset
uspto-grants-2001_08
Patent number
US06274610B1

Reaction notes

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