4-(Trifluoromethyl)aniline → 1,1-Dimethylethyl N-[4-(trifluoromethyl)phenyl]carbamate

HRID 1270791Notes

Reaction equation

HRID 1270791 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12](=O)([O:18]C(C)(C)C)[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]>C1COCC1>[C:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][CH:3]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:18]

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 112307451,1-Dimethylethyl N-[4-(trifluoromethyl)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-aminobenzotrifluoride (100 g, 0.62 mol) and di-tert-butyl carbonate (150 g, 0.69 mol) in anhydrous THF (400 mL) is heated at reflux temperature for 6 hours and then cooled to room temperature. Most of the solvent is removed using a rotary evaporator and the non-volatile material that remains is triturated with water (1000 mL) to form a solid. The solid is isolated by filtration and washed with additional water (500 mL), then washed with hexanes (500 mL) to give 4-(BOC-amino)benzotrifluoride (m.p. 123–124° C.).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 6 hours
  3. customMost of the solvent is removed
  4. customa rotary evaporator
  5. customthe non-volatile material that remains is triturated with water (1000 mL)
  6. customto form a solid
  7. customThe solid is isolated by filtration
  8. washwashed with additional water (500 mL)
  9. washwashed with hexanes (500 mL)

Sources & evidence

ORD record
ord-1024eb48a5714d6892abb8a1cd966078
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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