Sodium Hydroxide → 1-(4-chlorobutyl)-1H-benzotriazole
Reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[OH-].[Na+].[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1Participants
Conditions
- Temperature
- 60 °C
Procedure
Benzotriazole (11.9 g, 0.10 mol) is dissolved into 100 ml of 30% wt. sodium hydroxide, 4-chlorobromobutane (34.3 g, 0.20 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. Then the reaction solution was cooled down to ambient temperature, 100 ml of dichloromethane was added for extraction and liquid separation. To the aqueous phase, 100 of dichloromethane was added for extraction. Organic phases were mixed, washed with 100 ml of saturated saline. Liquid was separated, and organic phase was evaporated to dryness to produce oily product. Oily products were separated and purified by chromatography with neutral Al2O3, and eluted with dichlormethane to produce 17.0 g of 1-(4-chlorobutyl)-1H-benzotriazole, with a yield of 81.0%.
Workup
- additionare added
- additionmixed for 5 min
- temperatureThen the reaction solution was cooled down to ambient temperature
- additionOrganic phases were mixed
- washwashed with 100 ml of saturated saline
- customLiquid was separated
- customorganic phase was evaporated to dryness
- customto produce oily product
- customOily products were separated
- custompurified by chromatography with neutral Al2O3
- washeluted with dichlormethane
Sources & evidence
- ORD record
- ord-32e5225b7fa443c8ab013f6803395a70
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09415047B2
Reaction notes
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