Hydrochloric Acid → HCID 59430102, compound

HRID 505456Notes

Reaction equation

HRID 505456 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].Cl.N([O-])=O.[Na+].[N-:19]=[N+:20]=[N-].[Na+]>O.ClCCl>[CH3:13][O:12][C:8]1[CH:7]=[C:5]([N:6]=[N+:19]=[N-:20])[CH:4]=[C:3]([O:2][CH3:1])[C:9]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 322853,4,5-TrimethoxyanilineHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 59430102HCID 59430102, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3,4,5-Trimethoxyaniline (1.83 g; 10 mmol) is added to a 100 mL flask containing water (20 mL) and HCl (conc. aqueous solution, 5 mL). The solution is chilled to 0° C. and a solution of sodium nitrite (830 mg; 12 mmol) in water (5 mL) is added. The solution is stirred at 0° C. for 30 minutes, and then a solution of sodium azide (1.3 g; 20 mmol) in water (5 mL) is added. After another 30 minutes of stirring, dichloromethane is added (20 mL) and the organic phase was collected and filtered through a plug of silica, dried over magnesium sulfate and the solvent was evaporated to give approximately two grams of 3,4,5-trimethoxyphenyl azide.

Workup

  1. stirringAfter another 30 minutes of stirring
  2. customthe organic phase was collected
  3. filtrationfiltered through a plug of silica
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-102d64eb39e1477bb05574045fc6577d
Source dataset
uspto-grants-2010_08
Patent number
US07781462B2

Reaction notes

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