Sodium Hydroxide → HCID 136599349, compound

HRID 1522782Notes

Reaction equation

HRID 1522782 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[S:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:28]OC(OC)N(C)C.Cl.[CH3:37][O:38][NH2:39].[OH-].[Na+]>O.C(O)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:20]3[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=3)([C:16]([F:19])([F:18])[F:17])[S:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH:6]/[CH:28]=[N:39]/[O:38][CH3:37])=[O:5]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 78373Dimethylformamide dimethyl acetalHCID 521874O-Methylhydroxylamine hydrochlorideHCID 89444774HCID 89444774, compound

Product 1

HCID 136599349HCID 136599349, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-chloro-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]benzamide (50 mg) and N,N-Dimethylformamide dimethylacetal (1 mL) was refluxed under Argon for 30 min then the solution was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (0.48 mL) and a solution of O-methylhydroxylamine hydrochloride (2.8 eq.) and sodium hydroxide (6 eq.) in water (0.43 mL) and acetic acid (0.43 mL) was added. The solution was stirred at rt for one hour. 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 sodium sulfate and evaporated. Flash Chromatography eluting with Cyclohexane:EtOAc afforded 30 mg of the title compound.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionThe residue was dissolved in 1,4-dioxane (0.48 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 sodium sulfate
  7. customevaporated
  8. washFlash Chromatography eluting with Cyclohexane

Sources & evidence

ORD record
ord-bbac1c2b12b24ea5b61c28625a14454d
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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