Hydrochloric Acid → 2-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid N-cyanamide

HRID 235545

Reaction equation

[OH-].[K+].[N:3]#[C:4][NH2:5].[F:6][C:7]([F:28])([F:27])[C:8]1[CH:26]=[CH:25][C:11]([O:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1.Cl>O.CC(C)=O>[C:4]([NH:5][C:19](=[O:20])[CH:18]([O:17][C:16]1[CH:15]=[CH:14][C:13]([O:12][C:11]2[CH:25]=[CH:26][C:8]([C:7]([F:28])([F:6])[F:27])=[CH:9][CH:10]=2)=[CH:24][CH:23]=1)[CH3:22])#[N:3]

Participants

Conditions

Temperature: 10 °C

Procedure

10.4 g (0.1575 mole) of 85% potassium hydroxide are dissolved in 75 ml of water. 3.5 g (0.0825 mole) of cyanamide are added at 20° C. and the clear, colourless solution is cooled to 10° C. Then a solution of 25.8 g (0.075 mole) of 2-[4-(4-trifluoromethylphenoxy)phenoxy]propionyl chloride in 15 ml of acetone is added dropwise such that the temperature does not exceed 15° C. After the reaction mixture has been stirred for 45 minutes at this temperature, 9 g (0.09 mole) of 37% aqueous hydrochloric acid are added dropwise at 5° C. The product precipitates as an oil which crystallises on standing over 30 minutes. The colourless crystals are isolated by filtration, washed with water, dried over phosphorous pentoxide, affording 24.9 g (95.0% of theory) of 2-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid N-cyanamide with a melting point of 125°-127° C.

Workup

customdoes not exceed 15° C
additionare added dropwise at 5° C
customThe product precipitates as an oil which
customcrystallises
customThe colourless crystals are isolated by filtration
washwashed with water
dry with materialdried over phosphorous pentoxide

Sources & evidence

ORD record: ord-6a03fdb5a77b486599e7eab7f8ffd938
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04640703

Linked notes

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