Water → HCID 14478617, compound

HRID 345452Notes

Reaction equation

HRID 345452 reaction equation
[OH-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[C:16](\[CH2:22]OS(C2C=CC(C)=CC=2)(=O)=O)/[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=1.O>CN1CCCC1=O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[C:16](\[CH2:22][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)/[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 14798Sodium HydroxideHCID 86745160HCID 86745160, compound

Product 1

HCID 14478617HCID 14478617, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
50 °C

Procedure

9.2 g of sodium hydroxide are added to a solution of 16.8 g of 1,2,4-triazole in 150 ml of N-methylpyrrolidone and the mixture is heated at 50° C. for 30 minutes. After the reaction mixture has been cooled to room temperature, 73.1 g of Z-1-(4-chlorophenyl)-2-(4-methylphenylsulfonyloxymethyl)-4,4-dimethylpent-1-ene, dissolved in 100 ml of N-methylpyrrolidone, are slowly added dropwise to the solution and stirring is carried out for 12 hours at room temperature. Thereafter, 200 ml of water are added and the mixture is extracted several times with methyl tert-butyl ether, and the organic phase is washed twice with water, dried over sodium sulfate and evaporated down. The remaining residue is chromatographed over silica gel using 9:1 n-hexane/ethyl acetate to give 38 g (71%) of Z-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-4,4-dimethylpent-1-ene, which can be crystallized from methyl tert-butyl ether/n-hexane (mp.: 81°-84° C., compound No. A1).

Workup

  1. temperatureAfter the reaction mixture has been cooled to room temperature
  2. additionare slowly added dropwise to the solution
  3. extractionthe mixture is extracted several times with methyl tert-butyl ether
  4. washthe organic phase is washed twice with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated down
  7. customThe remaining residue is chromatographed over silica gel using 9:1 n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-6548dd59e8f74024adcc5b7f9d30004f
Source dataset
uspto-grants-1991_10
Patent number
US05057531

Reaction notes

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