Acetic Acid → HCID 136380330, compound

HRID 1161761Notes

Reaction equation

HRID 1161761 reaction equation
[OH:1][CH:2]=[C:3]([C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=CN=1)=[O:5].ClC1C=C[C:23]([NH2:24])=CC=1.C(O)(=O)C.[OH-].[Na+]>CS(C)=O>[OH:1][CH:2]=[C:3]([C:13]1[O:17][N:16]=[C:15]([CH3:18])[CH:14]=1)[C:4]([NH:6][C:7]1[CH:23]=[N:24][CH:10]=[CH:11][CH:12]=1)=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78124-ChloroanilineHCID 14798Sodium HydroxideHCID 136380314HCID 136380314, compound

Product 1

HCID 136380330HCID 136380330, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

General method for the synthesis of α-[4-(chlorophenylamino)methylene]-3-methyl-N-pyridyl-5-isoxazoleacetamide: α-Hydroxymethylene-3-methyl-N-pyridyl-5-isoxazoleacetamide (0.25 g, 1.0 mmol) was stirred with 4-chloroaniline (0.13 g, 1.0 mmol) and acetic acid (200 μL) in DMSO (3 mL) at rt for 24 h. The resulting solution was mixed with 10 mL of an aqueous 0.5 N NaOH solution and extracted with CH2Cl2. The organic layer was dried over Na2SO4 filtered and concentrated. The residue was then recrystallized from MeOH.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was then recrystallized from MeOH

Sources & evidence

ORD record
ord-059a76e2173c4da9a6b7f881c1510dcd
Source dataset
uspto-grants-2010_10
Patent number
US07820663B2

Reaction notes

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