4-Ethynylbenzonitrile → HCID 67515597, compound

HRID 1468173Notes

Reaction equation

HRID 1468173 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]=[N+:12]=[N-:13])[CH:5]=1.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1)#[N:16].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>ClCCl.C(OCC)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH:24]=[C:23]([C:20]3[CH:21]=[CH:22][C:17]([C:15]#[N:16])=[CH:18][CH:19]=3)[N:13]=[N:12]2)[CH:5]=1

Participants

7

Reactant 3

HCID 45472454-EthynylbenzonitrileHCID 11769343HCID 11769343, compoundHCID 23667548Sodium Ascorbate

Product 1

HCID 67515597HCID 67515597, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Treat a solution of 3-azidomethyl-benzoic acid methyl ester (0.4 g, 2.1 mmol) and 4-cyanophenylacetylene (0.25 g, 2.00 mmol) in 1 mL of dichloromethane with 1 mL of 0.1 M aqueous copper (II) sulfate solution and sodium ascorbate (0.06 g, 0.30 mmol). Stir at room temperature overnight, dilute the reaction with CH2Cl2 and wash 3 times with H2O. Dry the organic layer over sodium sulfate, filter and concentrate to afford a solid. Suspend the residue in diethyl ether and filter to give 0.53 g, 84% yield of 3-[4-(4-cyano-phenyl)-[1,2,3]triazol-1-ylmethyl]-benzoic acid methyl ester.

Workup

  1. additiondilute
  2. washwash 3 times with H2O
  3. dry with materialDry the organic layer over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto afford a solid
  7. filtrationfilter

Sources & evidence

ORD record
ord-36b1410c485b4acc8ccd778605ebfabb
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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