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Sodium Hydroxide → 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-thiazol-3-yl]-N-[(E)-ethoxyiminomethyl]-2-methylbenzamide

HRID 1522783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1522783
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[S:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:28]OC(OC)N(C)C.Cl.[CH2:37]([O:39][NH2:40])[CH3:38].[OH-].[Na+]>O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:25])([F:27])[F:26])[S:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:20]/[CH:28]=[N:40]/[O:39][CH2:37][CH3:38])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
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Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 78373Dimethylformamide dimethyl acetalHCID 894445764-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzamide

Produkt 1

HCID 1365993674-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-thiazol-3-yl]-N-[(E)-ethoxyiminomethyl]-2-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzamide (200 mg) and N,N-Dimethylformamide dimethylacetal (4 mL) was refluxed under Argon for one hour then the solution was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (2 mL) and a solution of O-ethylhydroxylamine hydrochloride (2.8 eq.) and sodium hydroxide (6 eq.) in water (1.6 mL) and acetic acid (1.6 mL) was added. The solution was stirred at rt for 10 minutes. It was then quenched by addition of water and extracted with methyl tert-butyl ether. The combined organic extracts were washed with brine, dried over magnesium sulfate and evaporated. Flash Chromatography eluting with Cyclohexane:EtOAc afforded 237 mg of the title compound.

Aufarbeitung

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionThe residue was dissolved in 1,4-dioxane (2 mL)
  3. customIt was then quenched by addition of water
  4. extractionextracted with methyl tert-butyl ether
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. washFlash Chromatography eluting with Cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-aae3819e03b24a4191bbd934034b74f8
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09078444B2

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