Chlorosuccinimide → 4-Amino-3-chloro-5-fluorobenzonitrile
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[F:10].C1C(=O)N([Cl:18])C(=O)C1>CC(O)=O>[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([C:6]#[N:7])=[CH:8][C:9]=1[Cl:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 4-amino-3-fluorobenzonitrile (184 mmol) and NCS (276 mmol) in AcOH (300 mL) was stirred at 70° C. for approximately 16 h. The mixture was concentrated. H2O was added to the residue and the solid product was filtered off and washed (sat. NaHCO3 and H2O). To eliminate H2O, THF was added and removed under reduced pressure to yield the desired product.
Workup
- concentrationThe mixture was concentrated
- additionH2O was added to the residue
- filtrationthe solid product was filtered off
- washwashed (sat. NaHCO3 and H2O)
- additionwas added
- customremoved under reduced pressure
Sources & evidence
- ORD record
- ord-306095c73a9a4bfabc97bcd9d3ba38ab
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440929B2
Reaction notes
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