5-Fluoro-2-nitrobenzotrifluoride → HCID 178525754, compound

HRID 1047380Notes

Reaction equation

HRID 1047380 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[NH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]1>C(#N)C.CN(C)C=O.O>[N+:12]([C:5]1[CH:4]=[CH:3][C:2]([NH:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]2)=[CH:7][C:6]=1[C:8]([F:11])([F:10])[F:9])([O-:14])=[O:13]

Participants

6

Reactant 2

HCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 178511567HCID 178511567, compound

Product 1

HCID 178525754HCID 178525754, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

5-Fluoro-2-nitrobenzotrifluoride (1.46 g, 7.0 mmol) and trans-4-aminocyclohexane carboxylic acid (1.0 g, 7.0 mmol) were dissolved in a mixture of acetonitrile (42 mL), dimethylformamide (21 mL), and water (7 mL). The resulting solution was heated to 85° C. and then maintained at this temperature overnight. After cooling to room temperature, the mixture was partly concentrated under vacuum, diluted with ethyl acetate (50 mL), and washed with water (30 mL). The aqueous phase was acidified to pH 4 by the addition of 1 M HCl. This formed a precipitate, which was isolated by filtration. The filtrate was extracted with ethyl acetate (2×10 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated under vacuum to afford a solid. Both solids were combined and dried under vacuum. The desired product was isolated as a yellow solid (2.4 g, quantitative yield).

Workup

  1. temperaturemaintained at this temperature overnight
  2. temperatureAfter cooling to room temperature
  3. concentrationthe mixture was partly concentrated under vacuum
  4. additiondiluted with ethyl acetate (50 mL)
  5. washwashed with water (30 mL)
  6. additionThe aqueous phase was acidified to pH 4 by the addition of 1 M HCl
  7. customThis formed a precipitate
  8. customwhich was isolated by filtration
  9. extractionThe filtrate was extracted with ethyl acetate (2×10 mL)
  10. dry with materialThe combined organic phases were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customto afford a solid
  14. customdried under vacuum

Sources & evidence

ORD record
ord-0face44a79dc495f9c6466255cbf5080
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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