Dimethylformamide → HCID 69215627, compound

HRID 2222031Notes

Reaction equation

HRID 2222031 reaction equation
Cl[CH2:2][C:3]1[CH:24]=[CH:23][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[O:12][C:13]=2[CH3:14])=[C:5]([O:25][CH3:26])[CH:4]=1.[CH2:27]([C:29]1[S:30][CH:31]=[C:32](/[CH:34]=[CH:35]/[C:36]2[C:37]([OH:47])=[N:38][N:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:40]=2)[N:33]=1)[CH3:28].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:27]([C:29]1[S:30][CH:31]=[C:32](/[CH:34]=[CH:35]/[C:36]2[C:37]([O:47][CH2:2][C:3]3[CH:24]=[CH:23][C:6]([O:7][CH2:8][C:9]4[N:10]=[C:11]([C:15]5[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=5)[C:18]#[N:19])[O:12][C:13]=4[CH3:14])=[C:5]([O:25][CH3:26])[CH:4]=3)=[N:38][N:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:40]=2)[N:33]=1)[CH3:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 69216863HCID 69216863, compoundHCID 178437612HCID 178437612, compound

Product 1

HCID 69215627HCID 69215627, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-{4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzonitrile (3.32 g), 4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-ol (2.95 g), potassium carbonate (1.37 g) and N,N-dimethylformamide (100 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic 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, v/v) to give 3-[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-1,3-oxazol-2-yl]benzonitrile (4.10 g, yield 72%) as colorless crystals. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 138-140° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran
  2. washThe organic 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, v/v)

Sources & evidence

ORD record
ord-02d46915bc0d42cdb44939ffd6c84072
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…