p-Toluenesulfonic acid → HCID 78165274, compound

HRID 333207Notes

Reaction equation

HRID 333207 reaction equation
[CH:1]([O:4][C:5]1[CH:30]=[CH:29][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=O)[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)[CH:12]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[NH2:31][NH:32][C:33]([NH2:35])=[S:34].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH:1]([O:4][C:5]1[CH:30]=[CH:29][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[N:31][NH:32][C:33]([NH2:35])=[S:34])[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)[CH:12]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 2723789ThiosemicarbazideHCID 86701426HCID 86701426, compound

Product 1

HCID 78165274HCID 78165274, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,3-bis-(4-isopropoxybenzoyl)benzene 21 (0.14 g, 0.39 mmol) was dissolved in anhydrous methanol (20 mL). The solution was heated at reflux for 15 min, and thiosemicarbazide (0.043 g, 0.47 mmol) and a catalytic amount of p-toluenesulfonic acid were added. After 10 h at reflux, the solvent was removed under vacuum and the resulting solid was further purified using flash chromatography (silica gel, hexanes:ethyl acetate, 50:50) to afford the desired 1,3-bis-(4-isopropoxybenzoyl)benzene thiosemicarbazone 22 as a white solid (0.05 g, 0.105 mmol, 27% yield); HRMS (ESI) calculated for C27H29N3O3SH+ (M+H) 476.2002, found 476.2005; HPLC retention time 18.440, 18.767 min.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 15 min
  3. temperatureAfter 10 h at reflux
  4. customthe solvent was removed under vacuum
  5. customthe resulting solid was further purified

Sources & evidence

ORD record
ord-34658904b0d94d8a9df0e595f1f04bde
Source dataset
uspto-grants-2014_11
Patent number
US08877967B2

Reaction notes

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