Phosphorus pentachloride → 4-amino-N-(6-chloropyridin-2-yl)-1,2,5-oxadiazole-3-carboximidoyl chloride

HRID 1663483Notes

Reaction equation

HRID 1663483 reaction equation
[NH2:1][C:2]1[C:3]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[N:11]=2)=O)=[N:4][O:5][N:6]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:18]>C1C=CC=CC=1>[NH2:1][C:2]1[C:3]([C:7]([Cl:18])=[N:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[N:11]=2)=[N:4][O:5][N:6]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 585583214-amino-N-(6-chloropyridin-2-yl)-1,2,5-oxadiazole-3-carboxamide

Product 1

HCID 585583764-amino-N-(6-chloropyridin-2-yl)-1,2,5-oxadiazole-3-carboximidoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-amino-N-(6-chloropyridin-2-yl)-1,2,5-oxadiazole-3-carboxamide (62 mg, 0.26 mmol) in benzene (5 mL) was treated with phosphorus pentachloride (0.12 g, 0.57 mmol) and stirred at reflux for 3 h. The reaction mixture was concentrated and rediluted with benzene and concentrated (3×) to give the desired product which was used immediately in the next step.

Workup

  1. temperatureat reflux for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. additionrediluted with benzene
  4. concentrationconcentrated (3×)

Sources & evidence

ORD record
ord-7afdddd66aa04a5cbe7d71254c320682
Source dataset
uspto-grants-2011_10
Patent number
US08034953B2

Reaction notes

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