Water → HCID 68232449, compound

HRID 1465818Notes

Reaction equation

HRID 1465818 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][O:13][CH2:14][CH2:15][NH:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH3:12][O:13][CH2:14][CH2:15][N:16]([CH3:17])[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:7])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 300977(2-Methoxyethyl)(methyl)amine

Product 1

HCID 68232449HCID 68232449, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
117.5 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (2.2 g, 12.7 mmol), (2-methoxy-ethyl)-methyl-amine (3.0 g, 33.7 mmol) and anhydrous potassium carbonate (1.93 g, 14 mmol) in N,N-dimethylacetamide (5 ml) was stirred at 115-120° C. under nitrogen for 2 days. Sample NMR analysis showed complete conversion of the starting material. The resultant mixture was then cooled to room temperature, poured into cold water (20 ml) and stirred vigorously and cooled at 5° C. overnight. The resulting yellow brown precipitate was collected by filtration, washed well with water then dried on the filter funnel. The resulting yellow brown solid was slurried in diethyl ether (20 mL), filtered, washed with additional diethyl ether, dried to afford N1-(2-methoxy-ethyl)-N1-methyl-4-nitro-benzene-1,3-diamine (2.1 g, 72%) as a yellow brown powder.

Workup

  1. stirringstirred vigorously
  2. temperaturecooled at 5° C. overnight
  3. filtrationThe resulting yellow brown precipitate was collected by filtration
  4. washwashed well with water
  5. customthen dried on the filter funnel
  6. filtrationfiltered
  7. washwashed with additional diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-768ad2989722457b9bd2f5e017f823a4
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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