Hydrochloric Acid → HCID 89487978, compound

HRID 570760Notes

Reaction equation

HRID 570760 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Br:18])[C:3]=1[N:19]([CH3:33])[C:20](=[O:32])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[C:22]=1[O:30][CH3:31].Cl>C(O)(C)C>[NH2:27][C:23]1[C:22]([O:30][CH3:31])=[C:21]([CH:26]=[CH:25][CH:24]=1)[C:20]([N:19]([C:3]1[C:2]([Br:1])=[CH:7][C:6]([C:8]([F:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:15])([F:16])[F:14])=[CH:5][C:4]=1[Br:18])[CH3:33])=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89488067HCID 89488067, compound

Product 1

HCID 89487978HCID 89487978, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of N-[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-2-methoxy-N-methyl-3-nitro-benzamide (described above) (0.500 g, 0.612 mmole) in 5 ml isopropanol, under argon atmosphere was added stannous chloride (SnCl2, 0.558 g, 2.94 mmole) followed by concentrated hydrochloric acid (0.250 ml). The suspension was stirred under reflux conditions for 2.25 hours. The mixture was then concentrated under vacuum. The residue was treated with water and the product was extracted twice with ethyl acetate. The combined organic extracts were washed with water and dried over sodium sulfate. Afer removal of the solvent, the residue was purified by flash chromatography over silica gel with a mixture of 15% ethyl acetate and 85% cyclohexane. The title compound was obtained as a yellow oil with a retention time of 1.15 min and a M+H+ mass peak of 581 (LC-MS method 6 described after the tables).

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. additionThe residue was treated with water
  3. extractionthe product was extracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. customAfer removal of the solvent
  7. customthe residue was purified by flash chromatography over silica gel with a mixture of 15% ethyl acetate and 85% cyclohexane

Sources & evidence

ORD record
ord-5977606bedfc4914904449a42f3fe865
Source dataset
uspto-grants-2015_05
Patent number
US09023873B2

Reaction notes

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