Hydrochloric Acid → HCID 58046333, compound

HRID 2359309Notes

Reaction equation

HRID 2359309 reaction equation
Cl.[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[C:16]([F:17])=[CH:15][C:11]([C:12](N)=[O:13])=[CH:10][C:9]=2[F:18])=[CH:5][C:4]=1[C:21]([F:24])([F:23])[F:22].[O:25]1CCOCC1>>[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[C:16]([F:17])=[CH:15][C:11]([C:12]([OH:25])=[O:13])=[CH:10][C:9]=2[F:18])=[CH:5][C:4]=1[C:21]([F:24])([F:23])[F:22]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86660882HCID 86660882, compound

Product 1

HCID 58046333HCID 58046333, compoundYield 59%

Conditions

Temperature
120 °C

Procedure

Hydrochloric acid (6M, 20 mL) was added to a solution of 4-(4-chloro-3-(trifluoromethyl)phenoxy)-3,5-difluorobenzamide (Preparation 86, 440 mg, 1.25 mmol) in dioxan (10 mL). The reaction mixture was stirred at 120° C. for 5 h. After cooling the solvent was removed in vacuo and the aqueous residue was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine (1×20 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with dichloromethane:methanol (from 98:2 to 85:15) then triturated with heptane to yield the title compound as a white solid (259 mg, 59%)

Workup

  1. temperatureAfter cooling the solvent
  2. customwas removed in vacuo
  3. extractionthe aqueous residue was extracted with ethyl acetate (2×30 mL)
  4. washThe combined organic layers were washed with brine (1×20 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified
  9. washeluting with dichloromethane
  10. custommethanol (from 98:2 to 85:15) then triturated with heptane

Sources & evidence

ORD record
ord-23eb5acc3bc04a1bb4fde046dcf66a07
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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