2-Fluoroaniline → HCID 18183268, compound
Reaction equation
[Br:1][CH:2]([CH3:6])[C:3](O)=[O:4].[F:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10].[CH:15]1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[F:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[N:10]([CH3:15])[C:3](=[O:4])[CH:2]([Br:1])[CH3:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Bromopropionic acid(3.4 g, 0.022 mol) and 2-fluoroaniline(3 g, 0.024 mol) were dissolved in 50 ml of chloroform and cooled to 0° C. A solution of dicyclohexylcarbodiimide(5 g, 0.024 mol) in 10 ml of chloroform was slowly injected through a syringe. A temperature of the reaction mixture was raised to room temperature and it was stirred for 1 hour. Solid remained during the reaction was filtered out and washed twice with 20 ml of chloroform. The filtrate was concentrated under reduced pressure and the crude product was purified by column chromatography (eluent; ethyl acetate/n-hexane=1/3) to afford 5 g of the target product.
Workup
- temperatureA temperature of the reaction mixture was raised to room temperature
- filtrationwas filtered out
- washwashed twice with 20 ml of chloroform
- concentrationThe filtrate was concentrated under reduced pressure
- customthe crude product was purified by column chromatography (eluent; ethyl acetate/n-hexane=1/3)
Sources & evidence
- ORD record
- ord-81ded47ad5b04d66ab9d4db4deeb5d12
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06486098B1
Reaction notes
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