Sodium Bicarbonate → HCID 178509311, compound

HRID 632524Notes

Reaction equation

HRID 632524 reaction equation
[NH2:1][C:2]1[C:3]([C:7](Cl)=[N:8][OH:9])=[N:4][O:5][N:6]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[F:19])[NH2:15].C(=O)(O)[O-].[Na+]>O>[NH2:1][C:2]1[C:3]([C:7](=[N:8][OH:9])[NH:15][C:14]2[CH:16]=[CH:17][C:18]([F:19])=[C:12]([Br:11])[CH:13]=2)=[N:4][O:5][N:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27792863-Bromo-4-fluoroanilineHCID 4040027(Z)-4-amino-N-hydroxy-1,2,5-oxadiazole-3-carbonimidoyl chloride

Product 1

HCID 178509311HCID 178509311, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-Amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride (33.8 g, 208 mmol) was mixed with water (300 mL). At 60° C., 3-bromo-4-fluoroaniline (Sigma-Aldrich) (43.6 g, 229 mmol, 1.1 equiv.) was added to the suspension with stirring for 10 min. A solution of sodium bicarbonate (26.3 g, 313 mmol, 1.5 equiv.) in water (300 mL) was added over 15 min with stirring at 60° C. After stirring 20 min, LCMS indicated reaction completion. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate (2×300 mL). The combined ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to give the desired product (65 g, 99%) as an off-white solid, which was used in the subsequent reaction without further purification. C9H7BrFN5O2 (MW 316.09), LCMS (EI) m/e 316/318 (M++H).

Workup

  1. stirringwith stirring at 60° C
  2. stirringAfter stirring 20 min
  3. customreaction completion
  4. extractionextracted with ethyl acetate (2×300 mL)
  5. dry with materialThe combined ethyl acetate solution was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6e0ce7eb7caa4575b8cf1ee412e3f7c0
Source dataset
uspto-grants-2016_04
Patent number
US09321755B2

Reaction notes

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