Epichlorohydrin → HCID 178513413, compound

HRID 480676Notes

Reaction equation

HRID 480676 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](=[N:8][OH:9])[NH2:7].[OH-].[K+].[CH2:17]([CH:19]1[O:21][CH2:20]1)Cl>CS(C)=O.O>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][O:9][CH2:17][CH:19]1[O:21][CH2:20]1)=[NH:7]

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 609330N'-hydroxy-3-(trifluoromethyl)benzimidamide

Product 1

HCID 178513413HCID 178513413, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

50 g (0.245 mol) of m-trifluoromethyl-benzamidoxime and 33.7 g (0.6 mol) of potassium hydroxide was dissolved in a mixture of dimethyl sulphoxide and 170 ml of water, and the mixture was cooled to 0° C. 48 ml (0.6 mol) of epichlorohydrine was added, and the reaction mixture was stirred at 0° C. for 5 hours, then kept in a refrigerator overnight. Next day 250 ml of water was added, and the mixture was extracted with ethyl acetate (4×250 ml). The combined organic phases were washed with water, dried, treated with charcoal and evaporated to dryness, to yield m-trifluoromethyl-N-(2,3-epoxypropoxy)-benzamidine, as a colorless oil.

Workup

  1. customkept in a refrigerator overnight
  2. extractionthe mixture was extracted with ethyl acetate (4×250 ml)
  3. washThe combined organic phases were washed with water
  4. customdried
  5. additiontreated with charcoal
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f045275f9e19419980c3566f8a673be7
Source dataset
uspto-grants-2003_11
Patent number
US06653326B1

Reaction notes

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