Hydrochloric Acid → HCID 57947846, compound

HRID 409752Notes

Reaction equation

HRID 409752 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([NH:15][NH2:16])=[O:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[N:18]([O-])=O.[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([N:15]=[N+:16]=[N-:18])=[O:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 57947817HCID 57947817, compound

Product 1

HCID 57947846HCID 57947846, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of 5-(3-fluorophenyl)isoxazole-3-carbohydrazide (22.5 g, 101 mmol) in H2O (2000 mL) and HCl (2 N, 101 mL, 2.0 equiv.) at 0° C. was added a solution of sodium nitrite (13.9 g, 202 mmol, 2.0 equiv.) in H2O (100 mL). The suspension was stirred at RT for 16 h. The precipitate was filtered and washed with H2O. The solid was dried under high vacuum to give 5-(3-fluorophenyl)isoxazole-3-carbonyl azide as a yellow solid (20 g, 85%). LRMS (M+H+)m/z 179.0.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with H2O
  3. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-3353b7a20db74e3d906fc909b5213d55
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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