Hydrochloric Acid → (Z)-4-amino-N-hydroxy-1,2,5-oxadiazole-3-carbonimidoyl chloride

HRID 82705Notes

Reaction equation

HRID 82705 reaction equation
[ClH:1].[NH2:2][C:3]1[C:4]([C:8](=[N:10][OH:11])N)=[N:5][O:6][N:7]=1.N([O-])=O.[Na+]>O>[NH2:2][C:3]1[C:4]([C:8]([Cl:1])=[N:10][OH:11])=[N:5][O:6][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 559349HCID 559349, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 4040027(Z)-4-amino-N-hydroxy-1,2,5-oxadiazole-3-carbonimidoyl chlorideYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A solution of 3 M of hydrogen chloride in water (190 mL) was treated with 4-amino-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide [J. Heterocycl. Chem. (1965), 2, 253] (7.3 g, 0.051 mol) at 0° C. The reaction mixture was treated with enough 12 M hydrogen chloride (˜19 mL) to dissolve the solid and then treated with a solution of sodium nitrite (4.4 g, 0.063 mol) in water (24 mL) dropwise while maintaining an internal temperature at 0-5° C. with an ice/brine bath. The reaction mixture was stirred at 0° C. for 1.5 h and filtered to yield a beige solid. Purification of the crude mixture by preparative HPLC gave the desired product (1.7 g, 21%) as an off-white solid.

Workup

  1. dissolutionto dissolve the solid
  2. filtrationfiltered
  3. customto yield a beige solid
  4. customPurification of the crude mixture by preparative HPLC

Sources & evidence

ORD record
ord-305ae39245434cdeaf8bf1a6318069b2
Source dataset
uspto-grants-2014_09
Patent number
US08846726B2

Reaction notes

Loading…