N,N'-Dimethylethylenediamine → ethyl 3-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]benzoate

HRID 1809964

Reaction equation

HRID 1809964 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[N-:13]=[N+:14]=[N-:15].[Na+].[CH2:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[CH:26])=[CH:21][CH:20]=1)[CH3:18].CNCCNC.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>[Cu]I.C(OCC)(=O)C.CS(C)=O.O>[CH2:25]([C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:13]=[N:14][N:15]([C:2]3[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=3)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:18]=2)=[CH:20][CH:21]=1)[CH3:26]

Participants

9

Reactant 5

HCID 8070N,N'-DimethylethylenediamineHCID 33557Sodium AzideHCID 1424251-Ethyl-4-ethynylbenzeneHCID 143542Ethyl 3-iodobenzoateHCID 23667548Sodium Ascorbate

Product 1

HCID 67030215ethyl 3-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]benzoate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Procedure

A mixture of ethyl 3-iodobenzoate (4-1) (138 mg, 0.5 mmol), sodium azide (34 mg, 0.52 mmol), 1-ethyl-4-ethynylbenzene (4-2) (65 mg, 0.5 mmol), CuI (10 mg), MeNHCH2CH2NHMe (11 μL), sodium ascorbate (10 mg), DMSO-H2O (v/v 5:1, 1.5 mL) is stirred at room temperature for 2 hours. The reaction mixture is then poured into ethyl acetate (50 mL), washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered and evaporated. The residue is purified on silica gel (0-33% ethyl acetate in hexane) to give ethyl 3-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]benzoate as a white solid.

Workup

  1. washwashed with water (10 mL) and brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified on silica gel (0-33% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-04d8a6fc35784539b2a7b23ce7e955f3
Source dataset
uspto-grants-2013_01
Patent number
US08362050B2

Linked notes

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