Potassium Hydroxide → HCID 13090852, compound

HRID 358183Notes

Reaction equation

HRID 358183 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][N:4]([CH3:9])[C:5](=[O:8])[CH2:6][OH:7].[OH-].[K+].Cl[C:15]1[S:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][N:19]=1>C(#N)C>[F:1][C:2]([F:10])([F:11])[CH2:3][N:4]([CH3:9])[C:5](=[O:8])[CH2:6][O:7][C:15]1[S:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][N:19]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2531452-Chloro-5-phenyl-1,3,4-thiadiazoleHCID 13090851HCID 13090851, compound

Product 1

HCID 13090852HCID 13090852, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

12 g (0.07 mol) of N-(2,2,2-trifluoroethyl)-N-methyl-hydroxyacetic acid amide and 4.5 g of potassium hydroxide powder were dispersed in 100 ml of acetonitrile at 0° C., and a solution of 12 g of 2-chloro-5-phenyl-1,3,4-thiadiazole in 50 ml of acetonitrile was added at 10° C. The mixture was stirred at 30° to 40° C. for 15 hours and concentrated, the concentrate was diluted with water and the mixture was filtered. The crystalline product was recrystallized from isopropanol. 12 g (63% of theory) of N-(2,2,2-trifluoroethyl)-N-methyl-5-phenyl-1,3,4-thiadiazol-2-yl-oxyacetic acid amide of melting point 123° C. were obtained.

Workup

  1. concentrationconcentrated
  2. additionthe concentrate was diluted with water
  3. filtrationthe mixture was filtered
  4. customThe crystalline product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-61c58244c0ff4ad5a1557ed52458b515
Source dataset
uspto-grants-1984_08
Patent number
US04465504

Reaction notes

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