Morpholine → HCID 3691063, compound

HRID 1458710Notes

Reaction equation

HRID 1458710 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>S(Cl)(Cl)=O.CC(C)=O>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:5]=1[C:6]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 3691063HCID 3691063, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Dissolved in 20 ml of thionyl chloride were 5.0 g (24.8 mmol) of 2-nitro-5-chlorobenzoic acid, followed by heating for 1.5 hours under reflux. After the reaction, the reaction mixture was concentrated and the residue was dissolved in 10 ml of acetone. The thus-obtained solution was added dropwise to a solution of 4.7 ml (62 mmol) of morpholine in 20 ml of acetone, followed by stirring at room temperature for 2 hours. Subsequent to the reaction, the reaction mixture was concentrated and then extracted with ethyl acetate. The ethyl acetate layer was dried and then concentrated. The residue was recrystallized from ethyl acetate/n-hexane, whereby 5.64 g of the title compound were obtained as white powder (yield: 84%).

Workup

  1. temperatureby heating for 1.5 hours
  2. temperatureunder reflux
  3. customAfter the reaction
  4. concentrationthe reaction mixture was concentrated
  5. dissolutionthe residue was dissolved in 10 ml of acetone
  6. customSubsequent to the reaction
  7. concentrationthe reaction mixture was concentrated
  8. extractionextracted with ethyl acetate
  9. dry with materialThe ethyl acetate layer was dried
  10. concentrationconcentrated
  11. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-ea48f36149af41cb83d834006f7aed41
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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