Sodium Azide → HCID 18400150, compound

HRID 1019080Notes

Reaction equation

HRID 1019080 reaction equation
Cl[C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O>[N:16]([C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1)=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 18400142HCID 18400142, compound

Product 1

HCID 18400150HCID 18400150, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-chloro-2,4-dinitro-m-xylene (707 mg, 3.1 mmol), sodium azide (219 mg, 3.37 mmol) and N,N-dimethylformamide (10 mL) is heated at 80° C. for 45 minutes then cooled to room temperature, poured into ice/water and extracted with ethyl acetate (3×50 mL). The combined organic layers are dried (magnesium sulfate), filtered, and concentrated via rotary evaporation to provide 5-azido-2, 4-dinitro-m-xylene as a yellow/brown solid. (650 mg, 2.7 mmol), 10% palladium-on-carbon (100 mg) and 80% formic acid (20 mL) is heated to 80° C. for 30 minutes, cooled to room temperature, and filtered through a plug of silica gel (eluting with water). The filtrate is basified (˜pH 10) with 28% ammonium hydroxide and extracted with ethyl acetate (3×100 mL). The combined organic layers are dried (magnesium sulfate), filtered, and concentrated to afford 4,6-dimethyl-5-nitrobenzimidazole as a yellow oil.

Workup

  1. temperaturethen cooled to room temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers are dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-780ae268f59249e1858dba1be2936869
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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