Ethanamine, 2,2,2-trifluoro- → 2-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxy-N-(2,2,2-trifluoroethyl)acetamide

HRID 1022841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022841
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:30])[F:29])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17](/[CH:20]=[N:21]/[O:22][CH2:23][C:24](O)=[O:25])=[C:16]([CH3:27])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl.CN(C)CCCN=C=NCC.[F:44][C:45]([F:49])([F:48])[CH2:46][NH2:47]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:29])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17](/[CH:20]=[N:21]/[O:22][CH2:23][C:24]([NH:47][CH2:46][C:45]([F:49])([F:48])[F:44])=[O:25])=[C:16]([CH3:27])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

5

Edukt 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 467018012-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxyacetic acid2×

Produkt 1

HCID 467018032-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylphenyl]methylideneamino]oxy-N-(2,2,2-trifluoroethyl)acetamideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of [1-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-meth-(E)-ylideneaminooxy]-acetic acid (i.e. the product of Step 2, 200 mg) in CH2Cl2 (12 mL) was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (130 mg). After 15 min, 2,2,2-trifluoroethyl amine (64 μL, 80 mg) and N,N-4-dimethylaminopyridine (80 mg) was added and the mixture was stirred at room temperature over night. After concentration in vacuum, the residue was purified by flash chromatography on silica gel to obtain the title compound (100 mg, 43%).

Aufarbeitung

  1. concentrationAfter concentration in vacuum
  2. customthe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4be84f0f5bd1423ebb727f97d31c368f
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722673B2

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