2,6-Dichloro-4-nitroaniline → 2,6-Dichloro-4-nitrobenzonitrile

HRID 1486581Notes

Reaction equation

HRID 1486581 reaction equation
[Cu][C:2]#[N:3].N(OC(C)(C)C)=O.[Cl:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([Cl:22])[C:13]=1N>CS(C)=O>[Cl:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([Cl:22])[C:13]=1[C:2]#[N:3]

Participants

5

Reactant 3

HCID 74302,6-Dichloro-4-nitroanilineHCID 10906Tert-Butyl nitriteHCID 178418546HCID 178418546, compound

Product 1

HCID 155276272,6-Dichloro-4-nitrobenzonitrileYield 16.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of copper(I) cyanide (2.6 g, 29.0 mmol, Eq: 2) in DMSO (5 mL) was heated at 60° for 1 hr. Tert-butyl nitrite (5.98 g, 6.9 ml, 58.0 mmol, Eq: 4.00) and a solution 2,6-dichloro-4-nitroaniline (3 g, 14.5 mmol, Eq: 1.00) in DMSO (5 mL) was added and the reaction was stirred for 3 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate 3×. The organic extract was washed with brine and dried over sodium sulfate. Chromatography (200 g Analogix, 100% hex to 5% EtOAc/hex) gave 515 mg (16%) of desired product as a light brown solid.

Workup

  1. extractionextracted with ethyl acetate 3×
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-dbdae42ee7214683adff02aac6897225
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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