Hydrochloric Acid → 5-Chloro-N1-(4'-cyanophenyl)-2,4-dinitroaniline

HRID 1876450

Reaction equation

HRID 1876450 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)#[N:16].CC(C)([O-])C.[K+].Cl>CN(C)C=O>[Cl:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([CH:7]=1)[NH:21][C:20]1[CH:22]=[CH:23][C:17]([C:15]#[N:16])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 133964-AminobenzonitrileHCID 772861,3-Dichloro-4,6-dinitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 706973965-Chloro-N1-(4'-cyanophenyl)-2,4-dinitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-Dichloro-1,5-dinitrobenzene (II-1, 1.2 g, 5 mmol) and p-cyanoaniline (III-1, 0.59 g, 5 mmol) were dissolved in N,N-dimethylformamide (DFM, 10 ml). To the solution was added potassium tert-butoxide (1.4 g, 12.5 mmol) in batches in ice water bath. The mixture was allowed to react at room temperature for 45 minutes. The reaction liquid was poured into ice water. The pH value was adjusted to about 6 with dilute hydrochloric acid. The mixture was stirred for 30 minutes to precipitate a solid. The solid was filtered, washed with water to neutrality, dried, and separated on silica gel column (eluted with ethyl acetate: petroleum ether) to obtain a compound VI-1 (1.44 g, faint yellow solid). 1H NMR (CDCl3) δ ppm 7.41 (1H, s, ArH-6), 7.57 (2H, d, J=8.7 Hz, ArH-3′, 5′), 7.91 (2H, d, J=8.7 Hz, ArH-2′, 6′), 8.90 (1H, s, ArH-3), 10.07 (1H, s, NH).

Workup

  1. customto react at room temperature for 45 minutes
  2. customThe reaction liquid
  3. customto precipitate a solid
  4. filtrationThe solid was filtered
  5. washwashed with water to neutrality
  6. customdried
  7. customseparated on silica gel column (eluted with ethyl acetate: petroleum ether)
  8. customto obtain a compound VI-1 (1.44 g, faint yellow solid)

Sources & evidence

ORD record
ord-3438de63c1f34272bac3be02e2cce82c
Source dataset
uspto-grants-2012_11
Patent number
US08309602B2

Linked notes

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