Sodium Hydroxide → 1-(3-chlorobutyl)-6-cyano-1H-benzotriazole

HRID 1482657Notes

Reaction equation

HRID 1482657 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[N:9][NH:8][C:7]=2[CH:11]=1)#[N:2].[OH-].[Na+].[Cl:14][CH:15]([CH3:19])[CH2:16][CH2:17]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:14][CH:15]([CH3:19])[CH2:16][CH2:17][N:8]1[C:7]2[CH:11]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[N:10]=[N:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 22644751HCID 22644751, compoundHCID 1785095371H-1,2,3-benzotriazole-5-carbonitrile

Product 1

HCID 1183868451-(3-chlorobutyl)-6-cyano-1H-benzotriazoleYield 38.8%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
60 °C

Procedure

6-cyano-1H-benzotriazole (15.9 g, 0.10 mol) is dissolved into 100 ml of 30% wt. sodium hydroxide, 3-chlorobromobutane (32.6 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 one for synthesis. The solution was separated and purified by HPLC to produce 9.1 g of 1-(3-chlorobutyl)-6-cyano-1H-benzotriazole, with a yield of 32.6%.

Workup

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

Sources & evidence

ORD record
ord-aa82ebc9b3624d65b12f5af0fa5b162c
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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