Methylamine → [2-(2-Chloro-6-nitrophenyl)ethyl](methyl)amine

HRID 1743838Notes

Reaction equation

HRID 1743838 reaction equation
[CH3:1][NH2:2].Br[CH2:4][CH2:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:15]>C1COCC1>[Cl:15][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]=1[CH2:5][CH2:4][NH:2][CH3:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 222365982-(2-Bromoethyl)-1-chloro-3-nitrobenzene

Product 1

HCID 22236581[2-(2-Chloro-6-nitrophenyl)ethyl](methyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methylamine in THF (2 M, 200 mL) was added 2-(2-bromoethyl)-1-chloro-3-nitro-benzene (14.0 g, 0.053 mole) in a pressure bottle, the reaction mixture was stirred at 60° C. overnight and the solvent was removed. The solid residue was treated with sodium hydroxide (1 N, 100 mL) and the aqueous extracted with methylene chloride (2×100 mL). The combined organic layers were washed with water (100 mL), saturated sodium chloride (100 mL), dried (sodium sulfate) and concentrated to provide 11.0 g of the title compound as a light brown oil. 1H NMR (DMSO-d6): 7.70 δ (d, 1H); 7.60 δ (d, 1H); 7.35 δ (t, 1H); 3.15 δ (t, 2H); 2.90 δ (t, 2H); 2.60 δ (s, 3H); 1.60 δ (broad, 1H).

Workup

  1. customthe solvent was removed
  2. additionThe solid residue was treated with sodium hydroxide (1 N, 100 mL)
  3. extractionthe aqueous extracted with methylene chloride (2×100 mL)
  4. washThe combined organic layers were washed with water (100 mL), saturated sodium chloride (100 mL)
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d30ed15698de415f93e82deb2a33f94a
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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