2,6-Dichloroaniline → HCID 22136220, compound

HRID 1826803Notes

Reaction equation

HRID 1826803 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[H-].[Na+].Cl[C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16]>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH:4][C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16]

Participants

6

Reactant 3

HCID 118462,6-DichloroanilineHCID 24758Sodium hydrideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 22136220HCID 22136220, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2,6-Dichloroaniline (2.84 g, 17.5 mmol) was dissolved in DMSO (5 mL) and 60% NaH (0.60 g, 15 mmol) was added. The mixture was stirred 30 min and then 2-chloro-5-nitrobenzonitrile (0.91 g, 5.0 mmol) in DMSO (5 mL) was added. The reaction darkened and warmed to 50°. After cooling to 23° the reaction was diluted with EtOAc (200 mL) and washed with H2O (3×), satd. aq. NaCl, and dried (Na2SO4), and concentrated to afford 1.45 g (94%) of the title compound as an ivory colored powder. 1H NMR (400) MHz. δ: 8.49 (finely split doublet, 1), 8.20 (dd, 1), 7.51 (d,2), 7.34 (d, 2), 6.41 (d, 1).

Workup

  1. customThe reaction darkened
  2. temperaturewarmed to 50°
  3. temperatureAfter cooling to 23° the reaction
  4. washwashed with H2O (3×)
  5. dry with materialaq. NaCl, and dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-81a273262da040e3a56e9b13fbf50a35
Source dataset
uspto-grants-2006_05
Patent number
US07053098B1

Reaction notes

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