Hydrochloric Acid → HCID 59497828, compound

HRID 1917055Notes

Reaction equation

HRID 1917055 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)([OH:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Br:22])[C:3]=1[NH:23][C:24](=[O:34])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-])=O)[CH:26]=1.[Sn](Cl)Cl.Cl>C(O)(C)C>[NH2:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[C:24]([NH:23][C:3]1[C:4]([Br:22])=[CH:5][C:6]([C:8]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)([OH:13])[C:9]([F:12])([F:10])[F:11])=[CH:7][C:2]=1[Br:1])=[O:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 59497821HCID 59497821, compound

Product 1

HCID 59497828HCID 59497828, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-{2,6-dibromo-4-[1-(3,5-dichloro-phenyl)-2,2,2-trifluoro-1-hydroxy-ethyl]-phenyl}-3-nitro-benzamide (Example I7) (0.206 g, 0.32 mmol) in isopropanol (15 ml) was added tin(II) chloride (0.218 g, 1.15 mmol). The mixture was cooled to 0° C. and aqueous hydrochloric acid (concentrated) (0.263 ml) was added slowly. The reaction mixture was stirred at 80° C. for 0.5 hours. ⅓ of the total volume of isopropanol was evaporated. Water (100 ml) was added to the concentrated mixture and aqueous sodium hydroxide (5N) was added to adjust the pH to 9. The aqueous phase was extracted three times with ethyl acetate (3×50 ml). The combined organic extracts were washed with water and brine, dried over sodium sulfate, and then concentrated. The residue was used without further purification. 1H-NMR (400 MHz, CDCl3): 8.22 (s, 1H), 7.72 (m, 3H), 7.47 (s, 2H), 7.12 (m, 3H), 6.77 (d, 1H), 5.35 (s, 2H) ppm.

Workup

  1. custom⅓ of the total volume of isopropanol was evaporated
  2. additionWater (100 ml) was added to the concentrated mixture and aqueous sodium hydroxide (5N)
  3. additionwas added
  4. extractionThe aqueous phase was extracted three times with ethyl acetate (3×50 ml)
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was used without further purification

Sources & evidence

ORD record
ord-a92e632e1b1b4557bc1d98510cddb474
Source dataset
uspto-grants-2013_12
Patent number
US08618173B2

Reaction notes

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