2,4-Dichloroaniline → N-(2,4-Dichlorophenyl)formamide

HRID 517694Notes

Reaction equation

HRID 517694 reaction equation
N1([CH:10]=[O:11])C2C=CC=CC=2N=N1.[Cl:12][C:13]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:14]=1[NH2:15]>O1CCCC1>[Cl:12][C:13]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:14]=1[NH:15][CH:10]=[O:11]

Participants

4

Reactant 2

HCID 111232,4-DichloroanilineHCID 5767401H-Benzotriazole-1-carboxaldehyde

Product 1

HCID 89907N-(2,4-Dichlorophenyl)formamideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1H-1,2,3-benzotriazole-1-carbaldehyde (327 mg, 2.22 mmol, Sigma-Aldrich) was added to a solution of 2,4-dichloroaniline (300 mg, 1.85 mmol) in tetrahydrofuran (THF) (6 mL). The solution was heated to 60° C. and stirred for 22.5 h before concentrating in vacuo. The resulting solid was dissolved in DCM (30 ml), washed with 2M HCl (15 ml), the organic layer was passed through a hydrophobic frit and reduced in vacuo. Purification was carried out by silica column chromatography (Biotage SP4, gradient elution 0-100% EtOAc in iso-hexane) to yield the title compound (334 mg).

Workup

  1. concentrationbefore concentrating in vacuo
  2. dissolutionThe resulting solid was dissolved in DCM (30 ml)
  3. washwashed with 2M HCl (15 ml)
  4. customPurification
  5. washwas carried out by silica column chromatography (Biotage SP4, gradient elution 0-100% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-03817dbdcfdd4fddb916629078477a24
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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