N,N,N',N'-Tetramethylethylenediamine → 9,9'-(Buta-1,3-diyne-1,4-diyl)dianthracene

HRID 1837395Notes

Reaction equation

HRID 1837395 reaction equation
[C:1]([C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2)#[CH:2].CN(C)[CH2:19][CH2:20]N(C)C>CC(C)=O.[Cu]Cl>[CH:5]1[C:4]2[C:9](=[CH:10][C:11]3[C:16]([C:3]=2[C:1]#[C:2][C:7]#[C:6][C:5]2[C:4]4[C:3]([CH:1]=[C:20]5[C:19]=2[CH:15]=[CH:14][CH:13]=[CH:12]5)=[CH:16][CH:11]=[CH:10][CH:9]=4)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 41401999-ethynylanthracene

Product 1

HCID 234979689,9'-(Buta-1,3-diyne-1,4-diyl)dianthraceneYield 873%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 180AcetoneSolvent

Procedure

15 g (0.074 mol) of 9-ethynyl anthracene, 0.36 g (3.7 mmol) copper(I) chloride, 0.43 g (3.7 mmol) of N,N,N′,N′-tetramethylethylenediamine were put into a 500 ml round-bottomed flask equipped with a stirrer, and then dissolved in 200 ml of acetone. The resulting mixture was then vigorously stirred for two hours while purging oxygen gas, to give red-colored solid. After the reaction was completed, the solvent was mostly removed with a small amount remaining. The residue was then precipitated in 5% aqueous hydrochloric acid to obtain red-colored solid. The solid was filtered, washed sufficiently with water and ethanol, and then recrystallized from ethyl acetate, to give red-colored crystal. The red-colored crystal was recovered and then sufficiently dried in a vacuum oven at 40° C., to give 13 g (87.2% yield) of the desired product having a melting point of 280-282° C.

Workup

  1. customequipped with a stirrer
  2. customwhile purging oxygen gas
  3. customto give red-colored solid
  4. customthe solvent was mostly removed with a small amount
  5. customThe residue was then precipitated in 5% aqueous hydrochloric acid
  6. customto obtain red-colored solid
  7. filtrationThe solid was filtered
  8. washwashed sufficiently with water and ethanol
  9. customrecrystallized from ethyl acetate
  10. customto give red-colored crystal
  11. customThe red-colored crystal was recovered
  12. customsufficiently dried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-9467ce71c2684d2886b390ad4ea46957
Source dataset
uspto-grants-2004_08
Patent number
US06780950B2

Reaction notes

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