hydroxylamine-O-sulfonic acid → HCID 1487829, compound

HRID 1370091Notes

Reaction equation

HRID 1370091 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:9][CH:8]=1)=[O:6].NOS(O)(=O)=O.C([O-])(O)=O.[Na+]>CO>[N:13]1([C:10]2[CH:11]=[CH:12][C:7]([C:5]3[O:6][N:2]=[CH:3][CH:4]=3)=[CH:8][CH:9]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 76284hydroxylamine-O-sulfonic acid2×HCID 516892Sodium BicarbonateHCID 1487825HCID 1487825, compound

Product 1

HCID 1487829HCID 1487829, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-imidazol-1-ylphenyl)isoxazole was prepared by treating a solution of 3-dimethylamino-1-[(4-imidazol-1-yl)phenyl]propen-1-one (1.64 g, 6.8 mmol) in MeOH with hydroxylamine-O-sulphonic acid (831 mg, 7.35 mmol) at ambient temperature for 16 h. A further quantity of hydroxylamine-O-sulphonic acid (831 mg, 7.35 mmol) was added and stirring continued for 3 h. The reaction was then treated with saturated NaHCO3 solution, the resulting solution being collected by filtration and washed with water and diethyl ether to give the desired material (1.08 g) as a pink solid, m.p. 168°._δH (d6 DMSO) 8.67 (1H, d, J 1.8 Hz), 3.89 (1H, s), 8.03-7.99 (2H, m), 7.86-7.84 (3H, m), 7.14 (1H, s) and 7.10 (1H, d, J 1.9 Hz).

Workup

  1. filtrationthe resulting solution being collected by filtration
  2. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-ab061d6947274a63ad57f3ec814ec0d8
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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