Chlorosuccinimide → 4-Amino-3-chloro-5-fluorobenzonitrile

HRID 59941

Reaction equation

HRID 59941 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

HCID 31398ChlorosuccinimideHCID 27564314-Amino-3-fluorobenzonitrile

Product 1

HCID 680399954-Amino-3-chloro-5-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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

  1. concentrationThe mixture was concentrated
  2. additionH2O was added to the residue
  3. filtrationthe solid product was filtered off
  4. washwashed (sat. NaHCO3 and H2O)
  5. additionwas added
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-306095c73a9a4bfabc97bcd9d3ba38ab
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Linked notes

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