Chloroform → 4-Amino-3,5-dichlorobenzonitrile

HRID 1590398Notes

Reaction equation

HRID 1590398 reaction equation
[CH:1]1[C:6]([C:7]#[N:8])=[CH:5]C=[C:3]([NH2:9])[CH:2]=1.S(Cl)([Cl:13])(=O)=O.[OH-].[Na+].[CH:17]([Cl:20])(Cl)Cl>>[Cl:13][C:2]1[CH:1]=[C:6]([CH:5]=[C:17]([Cl:20])[C:3]=1[NH2:9])[C:7]#[N:8]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 133964-AminobenzonitrileHCID 14798Sodium HydroxideHCID 24648Sulfuryl chloride

Product 1

HCID 5227064-Amino-3,5-dichlorobenzonitrile

Procedure

P-Aminobenzonitrile (11.8 g) (ex Aldrich) in dry chloroform (250 ml) under nitrogen was treated with sulphuryl chloride (4.05 g) (ex BDH) maintaining reaction temperature below 35°. After 2 hours at reflux the mixture was poured onto ice and made alkaline with 2M sodium hydroxide solution. Work up in the usual manner gave 3,5-dichloro-4-aminobenzonitrile (18.2 g) NMR 1H 7.35(2H,s), 4.70(2H,bs).

Workup

  1. temperaturemaintaining
  2. customreaction temperature below 35°
  3. temperatureAfter 2 hours at reflux the mixture
  4. additionwas poured onto ice

Sources & evidence

ORD record
ord-d369a0e018634f0a9d46da00629f21f9
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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