2-Aminobenzaldehyde → 2-(2,6-dichloro-3-nitro-phenyl)-N-(2-formyl-phenyl)-acetamide

HRID 270698

Reaction equation

HRID 270698 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([OH:15])=O.[NH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20]>S(Cl)(Cl)=O.ClCCl.CCOC(C)=O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([NH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20])=[O:15]

Participants

6

Reactant 2

HCID 682552-AminobenzaldehydeHCID 542654372,6-Dichloro-3-nitrophenylacetic acid

Product 1

HCID 598338822-(2,6-dichloro-3-nitro-phenyl)-N-(2-formyl-phenyl)-acetamideYield 88.6%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of (2,6-dichloro-3-nitro-phenyl)-acetic acid (0.90 g, 3.35 mmol) in thionyl chloride (15 mL) is refluxed for one hour. The solvent is removed by concentration and dry toluene is added to thoroughly remove thionyl chloride. To the solution of acid chloride in dry dichloromethane (30 mL) is added (drop-wise) a solution of 2-aminobenzaldehyde (0.365 g, 3.02 mmol) in dichloromethane (5.0 mL). The mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with EtOAc and washed with saturated K2CO3 and brine. The organic layer is dried, filtered and concentrated to give crude product (0.94 g, 88.6%).

Workup

  1. customThe solvent is removed by concentration and dry toluene
  2. additionis added to thoroughly remove thionyl chloride
  3. washwashed with saturated K2CO3 and brine
  4. customThe organic layer is dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-85921cc9266e4e75939cb8df0dbc30ea
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Linked notes

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