Ammonia → 3-(Iminomethoxymethyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole

HRID 4900Notes

Reaction equation

HRID 4900 reaction equation
Cl[C:2](Cl)(Cl)[C:3]1[N:7]=[C:6]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[O:5][N:4]=1.[NH3:20].[CH3:21][OH:22]>>[NH:20]=[CH:21][O:22][CH2:2][C:3]1[N:7]=[C:6]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[O:5][N:4]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 197971333-(Trichloromethyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole

Product 1

HCID 197971263-(Iminomethoxymethyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazoleYield 50.9%

Procedure

2.17 g of 3-(trichloromethyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole was added to 50 ml of methanol. An excess of ammonia gas was added with formation of bubble at 0° C. and then the mixture was stirred at room temperature for 4 hours. After evaporation of methanol, water was added to the residue. The aqueous solution was extracted with ethylacetate. After evaporation of ethylacetate, the residue was purified by column chromatography(hexane:ethylacetate) to provide 0.92 g of the desired product(yield: 50.9%).

Workup

  1. customof bubble at 0° C.
  2. customAfter evaporation of methanol, water
  3. additionwas added to the residue
  4. extractionThe aqueous solution was extracted with ethylacetate
  5. customAfter evaporation of ethylacetate
  6. customthe residue was purified by column chromatography(hexane:ethylacetate)

Sources & evidence

ORD record
ord-f7f78b9b17294d74a78dab97f5765fd7
Source dataset
uspto-grants-1993_09
Patent number
US05242890

Reaction notes

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