Dimethylformamide → HCID 69216429, compound

HRID 2222040Notes

Reaction equation

HRID 2222040 reaction equation
Cl[CH2:2][C:3]1[CH:25]=[CH:24][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)[O:12][C:13]=2[CH3:14])=[C:5]([O:26][CH3:27])[CH:4]=1.[CH2:28]([C:30]1[S:31][CH:32]=[C:33](/[CH:35]=[CH:36]/[C:37]2[C:38]([OH:48])=[N:39][N:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:41]=2)[N:34]=1)[CH3:29].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:28]([C:30]1[S:31][CH:32]=[C:33](/[CH:35]=[CH:36]/[C:37]2[C:38]([O:48][CH2:2][C:3]3[CH:25]=[CH:24][C:6]([O:7][CH2:8][C:9]4[N:10]=[C:11]([C:15]5[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=5)[O:12][C:13]=4[CH3:14])=[C:5]([O:26][CH3:27])[CH:4]=3)=[N:39][N:40]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:41]=2)[N:34]=1)[CH3:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23076418HCID 23076418, compoundHCID 178437612HCID 178437612, compound

Product 1

HCID 69216429HCID 69216429, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-2-(3-nitrophenyl)-1,3-oxazole (1.17 g), 4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-ol (0.892 g), potassium carbonate (0.415 g) and N,N-dimethylformamide (20 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with acetone-hexane (1:5-1:4-1:3, v/v) to give {4-({4-[({4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-2-(3-nitrophenyl)-1,3-oxazole (0.742 g, yield 38%) as colorless crystals. Recrystallization from ethyl acetate-diethyl ether gave pale-yellow prism crystals. melting point: 127-129° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with acetone-hexane (1:5-1:4-1:3

Sources & evidence

ORD record
ord-d1abddec8fdc4363a89ce9e1516c4196
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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