Water → HCID 67946076, compound

HRID 2051230Notes

Reaction equation

HRID 2051230 reaction equation
[OH-].[Na+].N1C=[CH:6][N:5]=[N:4]1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:18]([CH3:27])=[CH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[CH2:17][O:16]2)=[CH:11][CH:10]=1.O.[CH3:29][N:30]1CCCC1=O>>[N:5]1([CH2:17][C:15]([C:12]2[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=2)([OH:16])[C:18]([CH3:27])=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[CH:6]=[N:30][CH:29]=[N:4]1

Participants

6

Reactant 5

HCID 962WaterHCID 13387N-methyl-2-pyrrolidone2×HCID 14798Sodium HydroxideHCID 54036889HCID 54036889, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 67946076HCID 67946076, compoundYield 95%

Conditions

Temperature
50 °C

Procedure

12 g of sodium hydroxide are added to a solution of 70 g of triazole in 300 ml of N-methylpyrrolidone and the mixture is heated for 30 minutes at 50° C. Thereafter, 73 g of 2-(4-chlorophenyl)-2-(1-methyl-2-[2-chlorophenyl]-ethenyl)-oxirane, dissolved in 100 ml of N-methylpyrrolidone, are slowly added dropwise at room temperature. The reaction mixture is stirred for 15 hours at room temperature after which 300 ml of water are added to the solution and the mixture is extracted several times by shaking with methyl tert-butyl ether. The organic phase isolated is washed twice with water and then dried over sodium sulfate and evaporated down. Crystallization of the residue from methyl tert-butyl ether/n-hexane gives 85 g (95%) of 1-(1,2,4-triazol-1-ylmethyl)-1-(4-chlorophenyl)-2-methyl-3-(2-chlorophenyl)-propenol of melting point 141°-143° C.

Workup

  1. additionare slowly added dropwise at room temperature
  2. additionare added to the solution
  3. extractionthe mixture is extracted several times
  4. customThe organic phase isolated
  5. washis washed twice with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated down
  8. customCrystallization of the residue from methyl tert-butyl ether/n-hexane

Sources & evidence

ORD record
ord-5e7b33bbd31b46978765bad58586cda6
Source dataset
uspto-grants-1991_05
Patent number
US05017595

Reaction notes

Loading…