1H-1,2,4-Triazole → HCID 68846595, compound

HRID 29225Notes

Reaction equation

HRID 29225 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[O:5][CH:6]([CH2:19][CH3:20])[C:7]([NH:9][C:10]([CH3:18])([CH3:17])[C:11]#[C:12][CH2:13][CH2:14][CH2:15]Cl)=[O:8].C(=O)([O-])[O-].[K+].[K+].[NH:31]1[CH:35]=[N:34][CH:33]=[N:32]1.CCCCCC.C(OCC)(=O)C>CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[O:5][CH:6]([CH2:19][CH3:20])[C:7]([NH:9][C:10]([CH3:18])([CH3:17])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)=[O:8]

Participants

8

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 68849646HCID 68849646, compound

Product 1

HCID 68846595HCID 68846595, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide (0.59 g) in dry N,N-dimethylformamide (10 ml) containing anhydrous potassium carbonate (0.28 g) was added 1,2,4-triazole (0.10 g). The mixture was heated to 90° C. for 2.75 hours, cooled to ambient temperature, diluted with water and extracted with ethyl acetate (three times). The extracts were combined, washed with brine, dried over magnesium sulphate then evaporated under reduced pressure to give a yellow oil. The oil was fractionated by chromatography (silica; hexane/ethyl acetate, 2:1 by volume followed by ethyl acetate) to give the required product as a colourless oil, 0.16 g, 1H NMR (CDCl3) δ: 1.00-1.06(3H, t); 1.60(3H, s); 1.62(3H, s); 1.92-2.14(6H, m); 4.38-4.44(3H, m); 6.26(1H, s); 6.84(2H, s); 7.04(1H, s); 7.96(1H, s); 8.32(1H, s).

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with ethyl acetate (three times)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. customthen evaporated under reduced pressure
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-8f1f3b306b914e7fa27b6e94b11fb820
Source dataset
uspto-grants-2008_09
Patent number
US07420090B2

Reaction notes

Loading…