Benzenamine, 3,5-bis(trifluoromethyl)- → Phenyl [3,5-bis(trifluoromethyl)phenyl]carbamate
Reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].C(N(CC)C(C)C)(C)C.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>ClCCl>[C:29]1([O:28][C:26](=[O:27])[NH:6][C:5]2[CH:4]=[C:3]([C:2]([F:14])([F:15])[F:1])[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1Participants
Procedure
3,5-Bis-(trifluoromethyl)aniline (2.0 g, 8.7 mmol) was dissolved in dichloromethane (80 mL) and N,N-diisopropylethylamine (1.6 mL, 9.6 mmol) was added followed by slow addition of phenyl chloroformate (1.1 mL, 8.7 mmol). The resulting mixture was stirred at room temperature for 16 hours. The mixture was successively washed with 1N hydrochloric acid (3×100 mL), water (3×100 mL), a mixture of water and saturated aqueous sodium hydrogen carbonate (1:1, 2×100 mL) and a mixture of water and saturated aqueous sodium chloride (1:1, 3×100 mL), dried (MgSO4) and concentrated in vacuo. The residue was crystallised from heptane containing a little diethyl ether to afford 1.3 g (43%) of (3,5-bis-trifluoromethylphenyl)carbamic acid phenyl ester as a solid.
Workup
- washThe mixture was successively washed with 1N hydrochloric acid (3×100 mL), water (3×100 mL)
- additiona mixture of water and saturated aqueous sodium hydrogen carbonate (1:1, 2×100 mL)
- additiona mixture of water and saturated aqueous sodium chloride (1:1, 3×100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was crystallised from heptane containing a little diethyl ether
Sources & evidence
- ORD record
- ord-66ae1d6ffe444e1d9824c37a2af30a7a
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06503949B1
Reaction notes
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