Nitrite → HCID 21184677, compound

HRID 612679Notes

Reaction equation

HRID 612679 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[O:19][CH3:20])=[O:11].Cl.O.N([O-])=O.[N-:26]=[N+:27]=[N-].[Na+]>>[OH:1][C:2]1[CH:7]=[C:6]([N:8]=[N+:26]=[N-:27])[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[O:19][CH3:20])=[O:11]

Participants

5

Reactant 4

HCID 946NitriteHCID 33557Sodium AzideHCID 21184762HCID 21184762, compoundHCID 21885828Hydrate;hydrochloride

Product 1

HCID 21184677HCID 21184677, compoundYield 38%

Conditions

Temperature
0 °C

Procedure

The N-(2-hydroxy-4-aminophenyl)-N'-(2-methoxyphenyl)urea (300 mg. 1.17 mmol) was added to HCl/H2O (1.17 mL/2.34 mL), cooled to 0° C. Solution nitrite (80.7 mg, 1.17 mmol) was added to the reaction mixture. The reaction mixture was stirred at 0° C. for 30 minutes. The sodium azide (76 mg, 1.17 mmol) was added to reaction mixture and it was warmed to room temperature. The reaction mixture was stirred at room temperature for 18 hours. The 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 (125 mg, 38%). EI-MS m/z 300 (M+H)+

Workup

  1. temperaturewas warmed to room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 18 hours
  3. extractionThe 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-aefed0568bda4ee4aed7af5f01ffd34e
Source dataset
uspto-grants-1999_12
Patent number
US06005008

Reaction notes

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