Sodium Hydroxide → HCID 118386878, compound

HRID 1482599Notes

Reaction equation

HRID 1482599 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][CH2:17]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 960701-Bromo-5-chloropentaneHCID 178418385HCID 178418385, compound

Product 1

HCID 118386878HCID 118386878, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

Benzotriazole (11.9 g, 0.10 mol) is dissolved into 100 ml of 30% wt. sodium hydroxide, 5-chlorobromopentane (36.8 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 15.8 g of 1-(5-chloropentyl)-1H-benzotriazole, with a yield of 71.0%.

Workup

  1. additionare added
  2. additionmixed for 5 min
  3. temperatureThen the reaction solution was cooled down to ambient temperature
  4. additionOrganic phases were mixed
  5. washwashed with 100 ml of saturated saline
  6. customLiquid was separated
  7. customorganic phase was evaporated to dryness
  8. customto produce oily product
  9. customOily products were separated
  10. custompurified by chromatography with neutral Al2O3
  11. washeluted with dichlormethane

Sources & evidence

ORD record
ord-dcb7ba889f214273b33f9e80f08bb477
Source dataset
uspto-grants-2016_08
Patent number
US09415047B2

Reaction notes

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