N,N'-Dimethylethylenediamine → HCID 66616195, compound

HRID 2172155Notes

Reaction equation

HRID 2172155 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([O:18][CH3:19])=[O:17])=[N:9]2)=[CH:4][CH:3]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28].C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.C1(C)C=CC=CC=1>[O:28]=[C:24]1[CH2:25][CH2:26][CH2:27][N:23]1[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([O:18][CH3:19])=[O:17])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 66616129HCID 66616129, compound

Product 1

HCID 66616195HCID 66616195, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A 50 mL culture tube containing methyl 3-[1-(4-bromophenyl)-1H-[1,2,4]triazol-3-yl]benzoate (407 mg, 1.14 mmol), copper (I) iodide (10.8 mg, 0.057 mmol), pyrrolidin-2-one (121 mg, 1.42 mmol) and potassium carbonate (138 mg, 2.28 mmol) is evacuated and back charged with nitrogen. N,N′-Dimethylethylenediamine (10 mg, 0.12 mmol) and toluene (5 mL) are added, the tube is sealed with a PTFE cap, and the reaction mixture is heated to 110° C. with stirring for 12 h. The cooled reaction mixture is partitioned between water and ethyl acetate, and the organic extract is washed with water, dried over MgSO4, filtered and evaporated. The residual material is separated by column chromatography (silica gel, 1:20 methanol-dichloromethane) to provide methyl 3-{1-[4-(2-oxo-pyrrolidin-1-yl)-phenyl]-1H-[1,2,4]triazol-3-yl}-benzoate as a tan solid (380 mg, 92%).

Workup

  1. customis evacuated
  2. additionback charged with nitrogen
  3. customcap
  4. customThe cooled reaction mixture
  5. customis partitioned between water and ethyl acetate
  6. extractionthe organic extract
  7. washis washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe residual material is separated by column chromatography (silica gel, 1:20 methanol-dichloromethane)

Sources & evidence

ORD record
ord-7731d3eae16246bdbe2fac7cd99f06c6
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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