Water → HCID 58805191, compound

HRID 884409Notes

Reaction equation

HRID 884409 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[NH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[N:13]1([NH:12][C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20315N-AminomorpholineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 58805191HCID 58805191, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (2.5 g, 14 mmol), 4-aminomorpholine (4.4 g, 40 mmol), and K2CO3 (2.0 g, 14 mmol) in DMF (20 mL) was stirred at 120° C. for 18 h. The reaction mixture was cooled to room temperature and poured into water (150 mL). The crude solid product was collected by filtration, air dried, and purified by flash chromatography (silica gel, 4×15 cm, eluted with 20% ether in CHCl3) to yield the product as a yellow solid (0.7 g, 20%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe crude solid product was collected by filtration, air
  3. customdried
  4. custompurified by flash chromatography (silica gel, 4×15 cm, eluted with 20% ether in CHCl3)

Sources & evidence

ORD record
ord-1609c3e462ca41fca535cca11cb60f9f
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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