Morpholine → HCID 15708389, compound

HRID 1073066Notes

Reaction equation

HRID 1073066 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]=2[C:22](O)=[O:23])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S(Cl)(Cl)=O.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]=2[C:22]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:23])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 15708385HCID 15708385, compound

Product 1

HCID 15708389HCID 15708389, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

6.9 g of 1-(3,4-dimethoxyphenyl)-6-chloro-2-naphthoic acid are introduced into 50 ml of toluene, and 2.4 g of thionyl chloride are added thereto. The reaction mixture is heated to boiling point and then stirred for 5 hours under reflux. Then, at ~50°, 4.0 g of morpholine are added dropwise, and the mixture is again heated to boiling point and stirred for a further 3 hours under reflux. After cooling to room temperature, the reaction mixture is diluted with 100 ml of toluene, and the organic phase is washed three times with 250 ml of water each time, dried over sodium sulfate and filtered, and the solvent is evaporated off in vacuo. For purification, the oily residue is chromatographed over a column of silica gel using ethyl acetate. The title compound is obtained in the form of beige crystals. M.p. 157°-159°.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux
  4. temperaturethe mixture is again heated
  5. stirringstirred for a further 3 hours
  6. temperatureunder reflux
  7. washthe organic phase is washed three times with 250 ml of water each time
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent is evaporated off in vacuo
  11. customFor purification
  12. customthe oily residue is chromatographed over a column of silica gel

Sources & evidence

ORD record
ord-977809456a104df689e8f55107fd6cca
Source dataset
uspto-grants-1990_11
Patent number
US04968677

Reaction notes

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