Dimethylformamide → n-Octyl 1-benzotriazolyl ether

HRID 46588

Reaction equation

HRID 46588 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.CN(C)C=O.Cl[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>O>[N:2]1([O:1][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81421-ChlorooctaneHCID 11430Potassium CarbonateHCID 757711-Hydroxybenzotriazole

Product 1

HCID 12702944n-Octyl 1-benzotriazolyl ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 1-hydroxybenzotriazole (30.6 g), N,N-dimethylformamide (150 ml), 1-chlorooctane (32.7 g) and potassium carbonate (50 g) was heated at 135° C. for 0.5 hr. while stirring. The reaction mixture was poured into water and the resulting mixture was extracted with benzene. The benzene extract was dried and stripped of solvent by rotary evaporation and distillation to a pot temperature of 100 C. at a pressure of less than 0.1 mm of mercury. The product, n-octyl 1-benzotriazolyl ether was obtained as a clear yellow oil residue. The elemental analysis was as follows:

Workup

  1. extractionthe resulting mixture was extracted with benzene
  2. extractionThe benzene extract
  3. customwas dried
  4. customstripped of solvent by rotary evaporation and distillation to a pot temperature of 100 C

Sources & evidence

ORD record
ord-26af1a8e5e894fab9e9eb7ac561c0fff
Source dataset
uspto-grants-1979_11
Patent number
US04174285

Linked notes

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