Dimethylamine → HCID 18174736, compound

HRID 395614Notes

Reaction equation

HRID 395614 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.[CH3:26][NH:27][CH3:28].CC(=O)CC>C(OCC)(=O)C.CCCCCC>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:27]([CH3:28])[CH3:26])[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 674DimethylamineHCID 6569Methyl Ethyl KetoneHCID 109598002-Chloro-4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]oxazole

Product 1

HCID 18174736HCID 18174736, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 2-chloro-4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]oxazole (378 mg), an aqueous solution of dimethylamine (50%, 1.0 ml) and 2-butanone (10 ml) was stirred with heating under reflux for 12 hours. The reaction mixture was concentrated, the residue obtained was subjected to silica gel column chromatography, and 4-(4-chlorophenyl)-2-dimethylamino-5-[3-(2-methoxyphenoxy)propyl]oxazole was obtained as an oil (348 mg, 90%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction. Crystallization from acetone-hexane gave pale yellow prisms. Melting point 67-68° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 12 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue obtained

Sources & evidence

ORD record
ord-f9805e225baa477aad37e0afda45914c
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

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