Salicylaldehyde oxime → Methyl[5-(4-chlorophenyl)-3-methyl-1-(1,3-thiazol-5-yl)-1h-pyrazol-4-yl]acetate

HRID 563988Notes

Reaction equation

HRID 563988 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:6]([CH3:17])=[N:7][NH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1.Br[C:20]1[S:24][CH:23]=[N:22][CH:21]=1.C(=NO)C1C(=CC=CC=1)O.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:6]([CH3:17])=[N:7][N:8]([C:20]2[S:24][CH:23]=[N:22][CH:21]=2)[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 5460595-BromothiazoleHCID 178499523HCID 178499523, compound

Product 1

HCID 46899850Methyl[5-(4-chlorophenyl)-3-methyl-1-(1,3-thiazol-5-yl)-1h-pyrazol-4-yl]acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl[5-(4-chlorophenyl)-3-methyl-1H-pyrazol-4-yl]acetate (1.0 g, 3.77 mmol), 5-bromothiazole (0.526 g, 3.21 mmol), salicylaldoxime (0.103 g, 0.75 mmol), Cu2O (0.027 g, 0.18 mmol), Cs2CO3 (1.477 g, 4.53 mmol) and acetonitrile (4.8 ml) were introduced successively into a vessel which had been dried by heating and cooled under a stream of argon.

Workup

  1. customhad been dried
  2. temperatureby heating
  3. temperaturecooled under a stream of argon

Sources & evidence

ORD record
ord-027fbd6dad3f4aa8bcf31aef197b7529
Source dataset
uspto-grants-2011_11
Patent number
US08067611B2

Reaction notes

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