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

HRID 1522783Notes

Reaction equation

HRID 1522783 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aae3819e03b24a4191bbd934034b74f8
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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