1-Iodooctane → 2-Octyl-2H-benzo[d][1,2,3]triazole

HRID 1050702Notes

Reaction equation

HRID 1050702 reaction equation
[H-].[Na+].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[N:4]1.I[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[OH-].[Na+]>CN(C)C=O>[CH2:13]([N:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=[N:3]1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 123801-IodooctaneHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 178418385HCID 178418385, compound

Product 1

HCID 43716412-Octyl-2H-benzo[d][1,2,3]triazoleYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 4.00 g, 100 mmol) was added in small portions within 1 hours to a solution of benzotriazole (14.3 g, 120 mmol) and 1-iodooctane (25 g, 104 mmol) in anhydrous dimethylformamide (100 mL) stirred under argon at room temperature. After the addition, stirring was continued for 3 days. The reaction mixture was poured into ice/water (100 mL), treated with 2 N NaOH (100 mL) and extracted with hexane/ethyl ether (1:1, 3×200 mL). The extract was washed with water (200 mL), dried over anhydrous sodium carbonate, and the solvent was removed under reduced pressure. The residue was chromatographed using silica gel (500 g) and hexane/dichloromethane (1:1) as an eluent. The first fraction gave 2-octyl-2H-benzo[d][1,2,3]triazole (8.16 g, 35% yield) as an oily product. 1H NMR (400 MHz, CDCl3): δ 7.85 (m, 2H, benzotriazole), 7.37 (m, 2H, benzotriazole), 4.71 (t, J=7.3 Hz, 2H, octyl), 2.10 (m, 2H, octyl), 1.32 (m, 4H, octyl), 1.23 (m, 6H, octyl), 0.85 (t, J=7.3 Hz, 3H, octyl).

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. extractionextracted with hexane/ethyl ether (1:1, 3×200 mL)
  4. washThe extract was washed with water (200 mL)
  5. dry with materialdried over anhydrous sodium carbonate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was chromatographed

Sources & evidence

ORD record
ord-172a6f2dc62b4ca1af29af828de6e143
Source dataset
uspto-grants-2016_07
Patent number
US09382424B2

Reaction notes

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