4-(Pyridin-3-yloxy)benzohydrazide → HCID 178506232, compound

HRID 1994006Notes

Reaction equation

HRID 1994006 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([NH:14][NH2:15])=O)=[CH:10][CH:9]=2)[CH:2]=1.I.CS[C:21](=[NH:34])[NH:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=1>N1C=CC=CC=1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:21]2[NH:34][C:12]([C:11]3[CH:16]=[CH:17][C:8]([O:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[CH:9][CH:10]=3)=[N:14][N:15]=2)=[CH:24][C:25]=1[C:30]([F:31])([F:32])[F:33]

Participants

4

Reactant 2

HCID 591354344-(Pyridin-3-yloxy)benzohydrazideHCID 1785040011-[4-chloro-3-(trifluoromethyl)phenyl]-S-methylisothiourea hydroiodide

Product 1

HCID 178506232HCID 178506232, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(pyridine-3-yloxy)benzohydrazide (2.33 g, 10.2 mmol) was dissolved in ca. 70 mL of anhydrous pyridine and S-methyl N-[4-chloro-3-(trifluoromethyl)phenyl] isothiourea hydroiodide (4.04 g, 10.2 mmol) was added. The reaction mixture was refluxed for 18 hrs under Ar. The pyridine was removed in vacuo and the resulting residue was purified by silica gel chromatography using EtOAc as eluent to give the title product (0.56 g) as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hrs under Ar
  2. customThe pyridine was removed in vacuo
  3. customthe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-62fb29041b65433a86c17500e05951f8
Source dataset
uspto-grants-2010_01
Patent number
US07652051B2

Reaction notes

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