Sodium Hydroxide → HCID 59301265, compound

HRID 2236067Notes

Reaction equation

HRID 2236067 reaction equation
[C:1]1([N:7]2[N:11]=[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]3=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:16].C(O)(=O)C.[Br:21]Br.[OH-].[Na+]>ClCCl.O>[Br:16][C:15]1[C:9]2[C:10](=[N:11][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)[C:12]([Br:21])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24408Bromine2×HCID 1540962H-Benzotriazole, 2-phenyl-HCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 59301265HCID 59301265, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

2-phenyl-2H-benzotriazole (1.10 g, 5.1 mmol) was placed in a 1-neck 250-mL round bottomed flask. HBr/acetic acid (45% w/v, 20 mL) and bromine (0.79 mL, 15.3 mmol) were added. The flask was connected to a condenser and a scrubber. The mixture was heated in an oil bath at 150° C. for 0.5 hr. The solution was cooled to room temperature. Bromine (0.79 mL, 15.3 mmol) was again added to the reaction mixture and it was again heated to 150° C. for 1 hr. This step was repeated three more times. Water (200 mL) and dichloromethane (200 mL) were added to the reaction mixture followed by aqueous sodium hydroxide (1.5 M) solution to neutralize the acid. The organic layer was separated and dried with MgSO4. The solution was filtered and the solvent concentrated using a rotary evaporator. The solid was further dried under high vacuum at 60° C. for 2 hr. Yield: 78%.

Workup

  1. customThe flask was connected to a condenser
  2. temperatureThe solution was cooled to room temperature
  3. temperaturewas again heated to 150° C. for 1 hr
  4. customThe organic layer was separated
  5. dry with materialdried with MgSO4
  6. filtrationThe solution was filtered
  7. concentrationthe solvent concentrated
  8. customa rotary evaporator
  9. customThe solid was further dried under high vacuum at 60° C. for 2 hr

Sources & evidence

ORD record
ord-551e446261e548cdbeab5520f7647fac
Source dataset
uspto-grants-2010_05
Patent number
US07714099B2

Reaction notes

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