Morpholine → (3,4-Dinitrophenyl)(morpholino)methanone

HRID 2088368Notes

Reaction equation

HRID 2088368 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=O)([O-:3])=[O:2].S(Cl)(Cl)=O.C(N(CC)CC)C.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C1COCC1.CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:9])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8083Morpholine2×HCID 8471TriethylamineHCID 107093,4-Dinitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 13043973(3,4-Dinitrophenyl)(morpholino)methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,4-dinitrobenzoic acid (10 g, 47 mmol, 1 eq.) and DMF (0.1 mL) in THF (100 mL) was treated with thionyl chloride (4.5 mL, 62 mmol, 1.3 eq.) then heated to reflux for 2.5 h. The mixture was cooled in ice then triethylamine (10 mL, 71 mmol, 1.1 eq.) was added over 20 min, keeping internal temperature <5° C. Morpholine (6.2 mL, 71 mmol, 1.5 eq) was added to the resulting thick yellow suspension over 15 min, keeping internal temperature <10° C. The ice-bath was removed and the mixture allowed to warm to r.t. After 15 min, a further portion of morpholine (1 mL, 11 mmol, 0.24 eq.) was added and the mixture stirred overnight.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 2.5 h
  3. temperatureThe mixture was cooled in ice
  4. customtemperature <5° C
  5. customtemperature <10° C
  6. customThe ice-bath was removed

Sources & evidence

ORD record
ord-8eeafd4427c84cf2a410169e1b31c3b3
Source dataset
uspto-grants-2013_05
Patent number
US08435970B2

Reaction notes

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