5-Fluoro-2-nitrobenzotrifluoride → 4-(4-Nitro-3-trifluoromethyl-phenylamino)-cyclohexanol

HRID 1890387Notes

Reaction equation

HRID 1890387 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]([OH:22])[CH2:18][CH2:17]1>CS(C)=O.ClCCl>[N+:12]([C:5]1[CH:4]=[CH:3][C:2]([NH:15][CH:16]2[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]2)=[CH:7][C:6]=1[C:8]([F:11])([F:10])[F:9])([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 178511715HCID 178511715, compound

Product 1

HCID 433862244-(4-Nitro-3-trifluoromethyl-phenylamino)-cyclohexanol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
95 °C

Procedure

5-Fluoro-2-nitrobenzotrifluoride (400 mg, 1.91 mmol) and trans-4-aminocyclohexanol (220 mg, 1.91 mmol) are dissolved in dimethylsulfoxide (10 mL) and the reaction is then heated at 95° C. for 3.5 hours. After cooling to room temperature, the mixture is diluted with dichloromethane (15 mL) and washed with water (3×10 mL). The organic phase is collected and dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude product is recrystallised from petrol ether. The desired product is finally isolated as a yellow solid (84% yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (3×10 mL)
  3. customThe organic phase is collected
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is recrystallised from petrol ether

Sources & evidence

ORD record
ord-9623d8423d6244eb89a4c3da0adb3087
Source dataset
uspto-grants-2013_08
Patent number
US08507474B2

Reaction notes

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