p-Toluenesulfonic acid → HCID 13034467, compound

HRID 1759243Notes

Reaction equation

HRID 1759243 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][CH:14]3[N:9]([CH2:10][CH2:11][C:12](=O)[CH2:13]3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:19]1([N:18]=[C:12]2[CH2:11][CH2:10][N:9]3[CH:14]([CH2:15][CH2:16][CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:8]3)[CH2:13]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6115Aniline3×HCID 13034464HCID 13034464, compound

Product 1

HCID 13034467HCID 13034467, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The ketone (III) (5.25 g.) was dissolved in 100 ml. toluene and 2.13 g. aniline. A small amount of pTSA was added and the solution was refluxed overnight using a Dean-Starke trap. The solvent was removed in vacuo Yield, 6.9 g. The semi-solid still had some ketone present (IR spectrum) so the residue was recycled using 1 g. aniline. The reaction was worked up as above and the crude anil showed no ketone. Yield, 7.2 g. (6.97 g. theoretical; probably excess aniline present).

Workup

  1. temperaturethe solution was refluxed overnight
  2. customThe solvent was removed in vacuo
  3. customYield
  4. customYield

Sources & evidence

ORD record
ord-f4ab601c9cc14f90b6a0987490e89ad5
Source dataset
uspto-grants-1982_07
Patent number
US04339582

Reaction notes

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