1-Bromo-3-chloropropane → N-(3-chloropropyl)-6-methoxyl benzotriazole

HRID 1482655Notes

Reaction equation

HRID 1482655 reaction equation
[O:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[N:9][NH:8][C:7]=2[CH:11]=1)[CH3:2].[OH-].[Na+].[Cl:14][CH2:15][CH2:16][CH2:17]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:14][CH2:15][CH2:16][CH2:17][N:8]1[C:7]2[CH:11]=[C:3]([O:1][CH3:2])[CH:4]=[CH:5][C:6]=2[N:10]=[N:9]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 178488253HCID 178488253, compound

Product 1

HCID 118386874N-(3-chloropropyl)-6-methoxyl benzotriazoleYield 34.1%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
60 °C

Procedure

6-methoxyl-1H-benzotriazole (14.9 g, 0.10 mol) is dissolved into 100 ml of 30% wt. sodium hydroxide, 3-chlorobromopropane (31.4 g, 0.10 mol), tetrabutyl ammonium bromide (0.8 g) are added, and mixed for 5 min. The reaction solution is gradually heated to 60° C., stirred for reaction for 2 hours. Post treatment was performed based on common method two for synthesis. The solution was separated and purified by HPLC to produce 7.7 g of N-(3-chloropropyl)-6-methoxyl-benzotriazole, with a yield of 34.1%.

Workup

  1. additionare added
  2. additionmixed for 5 min
  3. customPost treatment was performed based on common method two for synthesis
  4. customThe solution was separated
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-cd05a18fe2454f89873256077c71ad4d
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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