Hydrochloric Acid → HCID 50940482, compound

HRID 587829Notes

Reaction equation

HRID 587829 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:4]=1[NH:20][C:21](=[O:36])[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[N:31][CH:30]=[N:29]2)=[C:24]([N+:33]([O-])=O)[CH:23]=1)[CH3:2].O.O.[Sn](Cl)Cl.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C(OCC)(=O)C>[NH2:33][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[N:28]1[CH:32]=[N:31][CH:30]=[N:29]1)[C:21]([NH:20][C:4]1[C:5]([CH3:19])=[CH:6][C:7]([C:9]([F:18])([C:14]([F:15])([F:16])[F:17])[C:10]([F:12])([F:13])[F:11])=[CH:8][C:3]=1[CH2:1][CH3:2])=[O:36]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 61436Stannous chloride dihydrateHCID 50940483HCID 50940483, compound

Product 1

HCID 50940482HCID 50940482, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N-[2-Ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-3-nitro-4-(1H-1,2,4-triazol-1-yl)benzamide (1.3 g) was dissolved in ethanol (20 ml). To the solution, tin (II) chloride dihydrate (1.4 g) and conc. hydrochloric acid (1 ml) were added and the mixture was stirred under heating at 60° C. for 4 hours. The reaction solution was neutralized with potassium carbonate while it is vigorously stirred with addition of ethyl acetate and water. The resulting precipitates were filtered using Celite, the aqueous phase was separated from the organic phase and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with brine and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain 3-amino-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-4-(1H-1,2,4-triazol-1-yl)benzamide (1.0 g, yield 97%).

Workup

  1. customThe resulting precipitates
  2. filtrationwere filtered
  3. customthe aqueous phase was separated from the organic phase
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtering off the drying agent
  8. distillationthe solvent was distilled off under reduced pressure
  9. customto obtain a crude product
  10. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-d47f522cfacd48b8b76b301d4f5ea587
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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