p-Toluenesulfonic acid → HCID 10789604, compound

HRID 376741Notes

Reaction equation

HRID 376741 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[CH2:13]([N:29]1[CH:33]=[CH:32][CH:31]=[CH:30]1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH2:13]([N:29]1[CH:30]=[CH:31][CH:32]=[C:33]1[C:3]1[C:4](=[O:11])[C:5]2[C:10]([C:1](=[O:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 85301,4-NaphthoquinoneHCID 15476404HCID 15476404, compound

Product 1

HCID 10789604HCID 10789604, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

6.32 millimol of 1,4-naphthoquinone and 3.16 millimol of N-hexadecylpyrrole were stirred in 50 ml of chloroform in a round-bottomed flask for 5 hours at room temperature, the reaction being catalysed by addition of a few milligrams of para-toluenesulphonic acid. The reaction medium was diluted with 50 ml of chloroform and then washed four times with 50 ml of water and finally with saturated aqueous NaCl solution. The resulting organic phase was dried over Na2SO4 and then concentrated under vacuum. The product 2-(1-hexadecyl-1H-pyrrol-2-yl)-[1,4]-naphthoquinone was thus isolated in a yield of 41% after purification by chromatography on a column of silica.

Workup

  1. washwashed four times with 50 ml of water
  2. dry with materialThe resulting organic phase was dried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aebcf2f0465049b59706faf6929ad136
Source dataset
uspto-grants-2000_02
Patent number
US06022379

Reaction notes

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