2,4-Dichlorobenzylamine → 2-(2,4-Dichlorobenzylamino)-1-(3-nitrophenyl)ethanone

HRID 45715

Reaction equation

HRID 45715 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=[O:4].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH2:22][NH2:23].C(N(CC)CC)C>C1COCC1>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH2:22][NH:23][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 14852,4-DichlorobenzylamineHCID 8471TriethylamineHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-one

Product 1

HCID 674600642-(2,4-Dichlorobenzylamino)-1-(3-nitrophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-bromo-1-(3-nitrophenyl)ethanone (10.0 g, 41.15 mmol, 1.00 equiv) in THF (150 mL), (2,4-dichlorophenyl)methanamine (7.16 g, 40.91 mmol, 1.00 equiv) and triethylamine (5.96 g, 59.01 mmol, 1.50 equiv). The resulting solution was stirred for 2 h at 25° C. The solids were filtered out. The filtrate was concentrated to dryness and used for next step, assuming theoretical yield.

Workup

  1. customInto a 250-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. filtrationThe solids were filtered out
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-4a1ec25d65af442db55f85cba8b5dbc7
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Linked notes

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