Benzaldehyde → HCID 86719464, compound

HRID 716672Notes

Reaction equation

HRID 716672 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10].[N-:14]=[N+:15]=[N-:16].[Na+].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C)[CH2:27][CH2:28]N>CN(C)C=O.[Cu]I.CC#N>[CH2:9]([N:11]([CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:27]1[N:14]=[N:15][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:28]=1)[CH2:12][CH3:13])[CH3:10]

Participants

9

Reactant 5

HCID 240BenzaldehydeHCID 8021DiethylamineHCID 11575IodobenzeneHCID 33557Sodium AzideHCID 66053N,N-Dimethylethylenediamine

Product 1

HCID 86719464HCID 86719464, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

An exemplary process to form a triazole product may include reacting calcium carbide, benzaldehyde, diethylamine, CuI and CH3CN for 18 hours at 80° C. (AAA-coupling), followed by addition of sodium azide, iodobenzene, CuI and N,N-dimethylethylenediamine in dimethyl formamide and stirred for 12 hours at 40° C. to obtain N-ethyl-N-(phenyl(1-phenyl-1H-1,2,3-triazol-4-yl)methyl)ethanamine after extraction and purification with 84% isolated yield.

Workup

  1. customfor 18 hours
  2. customat 80° C.

Sources & evidence

ORD record
ord-b07395077c3649b9ba455790d5cd4818
Source dataset
uspto-grants-2015_11
Patent number
US09193668B2

Reaction notes

Loading…