Aldoxime → HCID 89444774, compound

HRID 1522781Notes

Reaction equation

HRID 1522781 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[S:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=N[OH:30])C.[Cl-].[Cl-].[Cl-].[In+3].[OH-].[NH4+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH2:14][C:13]([C:19]3[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=3)([C:15]([F:18])([F:17])[F:16])[S:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]([NH2:5])=[O:30]

Participants

7

Reactant 4

HCID 7863AldoximeHCID 14923Ammonium HydroxideHCID 159675indium(III)chlorideHCID 89444718HCID 89444718, compound

Product 1

HCID 89444774HCID 89444774, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-chloro-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]benzonitrile (50 mg) in toluene (1 mL) were added acetaldehyde oxime (3 eq.) then indium trichloride (0.05 eq.). The mixture was stirred at 120° C. for 2 hours then it was allowed to cool to room temperature. The solution was diluted with ethyl acetate, then treated with ammonium hydroxide (2N). The mixture was washed two times with brine then the organic phase were collected and they were dried over magnesium sulfate, filtered and evaporated under vacuo to give 2-chloro-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]benzamide (50 mg).

Workup

  1. temperatureto cool to room temperature
  2. washThe mixture was washed two times with brine
  3. customthe organic phase were collected
  4. dry with materialthey were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuo

Sources & evidence

ORD record
ord-e19feebb6da14b88b2c5b2dcaabda1b6
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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