Urea → (2-Methoxy-ethyl)-(4-methoxy-3-nitro-phenyl)-methyl-amine

HRID 51838Notes

Reaction equation

HRID 51838 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH3:6].NC(N)=O.[N+:19]([O-])([O-:21])=[O:20].[K+]>S(=O)(=O)(O)O>[CH3:1][O:2][CH2:3][CH2:4][N:5]([C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[C:11]([N+:19]([O-:21])=[O:20])[CH:12]=1)[CH3:6]

Participants

5

Reactant 3

HCID 1176UreaHCID 24434Potassium NitrateHCID 118437404-methoxy-N-(2-methoxyethyl)-N-methylaniline

Product 1

HCID 22736970(2-Methoxy-ethyl)-(4-methoxy-3-nitro-phenyl)-methyl-amineYield 35.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a stirred solution of 600 mg (3.07 mmol) (2-methoxy-ethyl)-(4-methoxy-phenyl)-methyl-amine in 1.3 ml concentrated sulfuric acid at room temperature was added 222 mg (3.69 mmol) urea. After stirring for 1 h at room temperature, a solution of 342 mg (3.38 mmol) potassium nitrate in 0.6 ml concentrated sulfuric acid was added dropwise and stirring continued for a further 16 h. The mixture was then poured onto water amd extracted five times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/9 ethyl acetate/hexane) afforded 260 mg (35%) (2-methoxy-ethyl)-(4-methoxy-3-nitro-phenyl)-methyl-amine as an orange oil. ES-MS m/e (%): 241 (M+H+, 100).

Workup

  1. stirringstirring
  2. waitcontinued for a further 16 h
  3. additionThe mixture was then poured onto water
  4. extractionamd extracted five times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f42ccbe1767f4fed8adfe048a7432cda
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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