Water → 5-Morpholino-2-nitroaniline

HRID 884405Notes

Reaction equation

HRID 884405 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.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.O>CS(C)=O>[N:12]1([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 5967255-Morpholino-2-nitroanilineYield 43%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-chloro-2-nitrophenylamine (4.3 g, 25 mmol) and morpholine (4.4 mL, 500 mmol) in dimethylsulfoxide (DMSO) (25 mL) was stirred at 90° C. for 16 h. The reaction mixture was poured into water (500 mL) and the resulting precipitate was collected by vacuum filtration and recrystallized from methanol (300 mL) to yield the product as orange crystals (2.4 g, 43%). M.P. 177-178° C. (lit. 184-186° C.). See, Polymers 36:3401-3408 (1995).

Workup

  1. filtrationthe resulting precipitate was collected by vacuum filtration
  2. customrecrystallized from methanol (300 mL)

Sources & evidence

ORD record
ord-f5570118401d431380b1d8e4696362af
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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