Water → HCID 13304366, compound

HRID 370757Notes

Reaction equation

HRID 370757 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]([Cl:13])([Cl:12])[C:6]1[N:10]=[C:9](Cl)[S:8][N:7]=1.[CH3:14][N:15]([C:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=1)[C:16](=[O:19])[CH2:17][OH:18].O>C(C(C)=O)C(C)C>[CH3:14][N:15]([C:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=1)[C:16](=[O:19])[CH2:17][O:18][C:9]1[S:8][N:7]=[C:6]([C:5]([Cl:13])([Cl:12])[Cl:4])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 799301,2,4-Thiadiazole, 5-chloro-3-(trichloromethyl)-HCID 168937Lithium hydroxide, monohydrateHCID 54484327N-(Cyclohex-1-en-1-yl)-2-hydroxy-N-methylacetamide

Product 1

HCID 13304366HCID 13304366, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
0 °C

Procedure

3.1 g (0.07 mol) of lithium hydroxide hydrate are added in portions, at 0° C., to 16.7 g (0.07 mol) of 3-trichloromethyl-5-chloro-1,2,4-thiadiazole and 11.8 g (0.07 mol) of hydroxyacetic acid N-methyl-N-cyclohex-1-enylamide in 100 ml of methyl isobutyl ketone, and the mixture is stirred for 30 minutes at 0° C. and then overnight at 25° C. After water has been added, the reaction product which separates out as a solid is filtered off under suction, washed and dried. 22.0 g (84.8% of theory) of 3-trichloromethyl-1,2,4-thiadiazol-5-yl-oxyacetic acid N-methyl-N-cyclohexen-1-yl-amide are obtained in the form of beige-colored crystals of melting point 78° C.

Workup

  1. customovernight
  2. customat 25° C
  3. filtrationis filtered off under suction
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-5df05e4225974b2e83f5b6dc497ec804
Source dataset
uspto-grants-1985_07
Patent number
US04528379

Reaction notes

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