Methylamine → [2-(4-Chloro-2-nitrophenyl)ethyl](methyl)amine

HRID 1743870Notes

Reaction equation

HRID 1743870 reaction equation
[CH3:1][NH2:2].Br[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14]>C1COCC1>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][NH:2][CH3:1])=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 222365841-(2-Bromoethyl)-4-chloro-2-nitrobenzene

Product 1

HCID 22236591[2-(4-Chloro-2-nitrophenyl)ethyl](methyl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl amine in THF (2 M, 200 mL) was added 1-(2-bromo-ethyl)-4-chloro-2-nitro-benzene (17.5 g, 0.066 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 14.9 g of the title compound as a brown oil. 1H NMR (DMSO-d6): 7.95 δ (d, 1H); 7.67 δ (dd, 1H); 7.50 δ (t, 1H); 3.28 δ (broad, 1H); 2.85 δ (t, 2H); 2.64 δ (t, 2H); 2.20 δ (s, 3H).

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-ae46561ae6284e468a1c9b78c5a7e325
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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