Sulfuric Acid → 1-Azido-5-chloro-2,4-dimethoxybenzene

HRID 12438Notes

Reaction equation

HRID 12438 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[C:8]([O:16][CH3:17])=[CH:9][C:10]([O:14][CH3:15])=[C:11]([NH2:13])[CH:12]=1.N([O-])=O.[Na+].[N-:22]=[N+:23]=[N-].[Na+]>O>[N:13]([C:11]1[CH:12]=[C:7]([Cl:6])[C:8]([O:16][CH3:17])=[CH:9][C:10]=1[O:14][CH3:15])=[N+:22]=[N-:23]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 668075-Chloro-2,4-dimethoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 587310171-Azido-5-chloro-2,4-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Conditions

Temperature
0 °C

Procedure

To a solution of concentrated H2SO4 (5 mL) in water (15 mL), 5-chloro-2,4-dimethoxy-phenylamine (3 g, 16 mmol) was added, resulting a deep purple suspension. More water (15 mL) was then added and the mixture was cooled and stirred vigorously at 0° C. in an ice-salt bath. A solution of sodium nitrite (1.2 g, 17.4 mmol) in water (5 mL) was added slowly and a brown solution was obtained. This solution was stirred at this temperature for an hour. After that, a solution of sodium azide (1.2 g, 18.5 mmol) in water (10 mL) was followed and the solution turned grey. This solution was then stirred for an hour. The grey precipitations (1.0 g, 30%) formed were collected, washed with water and dried. Yellow solids formed in the filtrate were also collected, washed and dried. The second crop (1.47 g, 43%) turned to light grey quickly.

Workup

  1. customresulting a deep purple suspension
  2. temperaturethe mixture was cooled
  3. customa brown solution was obtained
  4. stirringThis solution was stirred at this temperature for an hour
  5. stirringThis solution was then stirred for an hour
  6. customThe grey precipitations (1.0 g, 30%)
  7. customformed
  8. customwere collected
  9. washwashed with water
  10. customdried
  11. customYellow solids formed in the filtrate
  12. customwere also collected
  13. washwashed
  14. customdried

Sources & evidence

ORD record
ord-71fdf134242643dab57ea5ca4a673cc1
Source dataset
uspto-grants-2010_06
Patent number
US07728016B2

Reaction notes

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