2,4-Dichlorobenzoyl chloride → HCID 45258955, compound

HRID 1818005Notes

Reaction equation

HRID 1818005 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:13]=1[Cl:12]

Participants

5

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 45258955HCID 45258955, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 500 mL, round-bottomed, one-necked flask equipped with a magnetic stir bar and a septum was added 2-amino-3-nitrophenol (4.25 g, 27.6 mmol), anhydrous CH2Cl2 (140 mL), 4-(dimethylamino)pyridine (3.37 g, 27.6 mmol) and 2,4-dichlorobenzoyl chloride (5.78 g, 3.87 mL, 27.6 mmol). The reaction mixture was allowed to stir at room temperature overnight. TLC analysis indicated the complete consumption of starting material. The reaction mixture was diluted with CH2Cl2 (300 mL) and the mixture was washed with H2O (2×200 mL), dried (Na2SO4), and concentrated to give 8.91 g (98.7%) of a yellow-orange solid. 1H NMR analysis indicated the material, I-113 was pure enough to carry on to the next step. 1H NMR (500 MHz, CDCl3).

Workup

  1. customTo a 500 mL, round-bottomed, one-necked flask equipped with a magnetic stir bar
  2. customthe complete consumption of starting material
  3. additionThe reaction mixture was diluted with CH2Cl2 (300 mL)
  4. washthe mixture was washed with H2O (2×200 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-397725855d914389b4a5f2125db34ddf
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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