Benzoyl chloride, 3-nitro- → 3-(4,5-dihydro-1H-imidazol-2-yl)amino-5-trifluoromethylhippuric acid
Reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)[C:6](=[O:12])[NH:7][CH2:8][C:9]([OH:11])=[O:10].[N+](C1C=C(C=C(C(F)(F)F)C=1)C(O)=O)([O-])=O.S(Cl)(Cl)=O.[N+](C1C=C(C=CC=1)C(Cl)=O)([O-])=O.C([N:59]1[CH2:63][CH2:62][N:61]=[C:60]1SC)(OC(C)(C)C)=O>CC#N>[NH:61]1[CH2:62][CH2:63][N:59]=[C:60]1[NH:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1)[C:6](=[O:12])[NH:7][CH2:8][C:9]([OH:11])=[O:10]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
To 3-amino-5-trifluoromethylhippuric acid hydrochloride [prepared according to Example M, Steps A and B substituting 3-nitro-5-trifluoromethylbenzoyl chloride (prepared from 3-nitro-5-trifluoromethylbenzoic acid (Lancaster) and thionyl chloride for M-nitrobenzoyl chloride in Example M, Step A] (3 g, 0.01 mole) in CH3CN (5 mL) was added the product from Example 472, Step A (2.2 g, 0.01 mole). The reaction was stirred at 35° C. for 3 days then at reflux for 4 hours. After cooling, the CH3CN was decanted off, the residue slurried several times in ether (ether decanted off) and then dried to yield 3-(4,5-dihydro-1H-imidazol-2-yl)amino-5-trifluoromethylhippuric acid.HCl (2.5 g) as a white solid.
Workup
- temperatureat reflux for 4 hours
- temperatureAfter cooling
- customthe CH3CN was decanted off
- customdried
Sources & evidence
- ORD record
- ord-a36c90cf6b1d4c1886bb714a962bd8fe
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06028223
Reaction notes
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