Sodium Azide → HCID 21184677, compound

HRID 323078Notes

Reaction equation

HRID 323078 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.[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[O:19][CH3:20])=[O:11]

Participants

5

Reactant 4

HCID 33557Sodium AzideHCID 21184762HCID 21184762, compoundHCID 21885828Hydrate;hydrochlorideHCID 23668193Sodium Nitrite

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. Sodium 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. 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 (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. 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-39604da5ed584906b0aa9203e6b5a583
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Reaction notes

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