Sodium Nitrate → HCID 21184698, compound

HRID 612716Notes

Reaction equation

HRID 612716 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([NH2:8])[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[I:19])=[O:11].Cl.O.[N+]([O-])([O-])=O.[Na+].[N-:27]=[N+:28]=[N-].[Na+]>>[OH:1][C:2]1[CH:7]=[C:6]([N:8]=[N+:27]=[N-:28])[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[I:19])=[O:11]

Participants

5

Reactant 4

HCID 24268Sodium NitrateHCID 33557Sodium AzideHCID 21184767HCID 21184767, compoundHCID 21885828Hydrate;hydrochloride

Product 1

HCID 21184698HCID 21184698, compoundYield 24.1%

Conditions

Temperature
0 °C

Procedure

The N-(2-hydroxy-4-aminophenyl)-N'-(2-iodophenyl)urea(77 mg, 0.21 mmol) was added to HCl/H2O (0.21 mL/0.42 mL), and cooled to 0° C. Sodium nitrate (14.5 mg, 0.21 mmol) was added to the reaction mixture. The reaction mixture was stirred at 0° C. for 30 minutes. Sodium azide (14 mg, 0.21 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 by 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 (20 mg, 24%). EI-MS m/z 396 (M+H)+.

Workup

  1. temperaturewas warmed to room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 18 hours
  3. extractionThen it was extracted with three times by 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-f8e095999b4f4c44a85f8c7f27945e44
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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