Methyl Ethyl Ketone → HCID 18174706, compound

HRID 395607Notes

Reaction equation

HRID 395607 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CC(=O)CC>O>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[O:3][C:4]=2[CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 8083MorpholineHCID 109598002-Chloro-4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]oxazole

Product 1

HCID 18174706HCID 18174706, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]oxazole (378 mg), morpholine (435 mg) and 2-butanone (10 ml) was stirred with heating under reflux for 2 hours. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (100 ml×2). The organic layer was washed with a 10% aqueous solution of citric acid (100 ml) and dried over anhydrous magnesium sulfate. After the organic layer was concentrated, the residue was recrystallized from ethyl acetate-hexane to give 4-(4-chlorophenyl)-2-(4-morpholinyl)-5-[3-(2-methoxyphenoxy)propyl]oxazole as pale yellow prisms (353 mg, 82%). Melting point 81-82° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate (100 ml×2)
  4. washThe organic layer was washed with a 10% aqueous solution of citric acid (100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationAfter the organic layer was concentrated
  7. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-60ea167b7a414825940638a312d173b6
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

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