Sodium Nitrate → HCID 21184628, compound

HRID 323119Notes

Reaction equation

HRID 323119 reaction equation
[OH:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Br:19])=[O:11].Cl.O.[N+]([O-])([O-])=O.[Na+].[N-:27]=[N+:28]=[N-].[Na+]>>[OH:1][C:2]1[C:7]([N:8]=[N+:27]=[N-:28])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Br:19])=[O:11]

Participants

5

Reactant 4

HCID 24268Sodium NitrateHCID 33557Sodium AzideHCID 21184806HCID 21184806, compoundHCID 21885828Hydrate;hydrochloride

Product 1

HCID 21184628HCID 21184628, compoundYield 71%

Conditions

Temperature
0 °C

Procedure

The N-(2-hydroxy-3-aminophenyl)-N′-(2-bromophenyl)urea(274 mg, 0.85 mmol) was added to HCl/H2O (0.85 mL/1.7 mL), cooled to 0° C. Sodium nitrate (58.6 mg, 0.85 mmol) was added to the reaction mixture. The reaction mixture was stirred at 0° C. for 30 minutes. Sodium azide (55 mg, 0.85 mmol) was added to reaction mixture and it was warmed to room temperature. The reaction mixture was stirred at room temperature for 18 hours then it was extracted with three times with ethyl acetate. The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure and chromatography of the resulting solid on silica gel (hexane:ethyl acetate; 5:1) gave product (210 mg, 71%). EI-MS m/z 349 (M+H)+.

Workup

  1. temperaturewas warmed to room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 18 hours
  3. extractionit was extracted with three times with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure and chromatography of the resulting solid on silica gel (hexane:ethyl acetate; 5:1)

Sources & evidence

ORD record
ord-f5823218254447ca9f0b92c6f52537df
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Reaction notes

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