p-Toluenesulfonic acid → HCID 19374693, compound

HRID 128572Notes

Reaction equation

HRID 128572 reaction equation
O1CCCO[CH:2]1[C:7]1[CH:11]=[CH:10][S:9][C:8]=1[S:12]([NH:15][NH2:16])(=[O:14])=[O:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.C(OCC)(=O)C>[S:12]1(=[O:14])(=[O:13])[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:2]=[N:16][NH:15]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22414510HCID 22414510, compound

Product 1

HCID 19374693HCID 19374693, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
56 °C

Procedure

The solid obtained in step A (2.4 g, 48 mmol) was dissolved in acetone (70 mL). p-Toluenesulfonic acid (0.20 g, 1 mmol) was added and the mixture was stirred at refluxing temperature (56° C.) for 2h. The solvent was evaporated, the residue obtained was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate (20 mL) and brine. The ethyl acetate layer was dried over MgSO4 and evaporated to a green solid which was flash chromatographed (silica, hexane-ethyl acetate gradient) to provide a white solid (1.62 g, 90%). mp:125°-127° C. Cl-MS m/e 189 (M+H)+. 1HNMR (DMSO-d6):δ:7.44 (1H, 1s, CH); 7.44 (1H, d, J=5.0 Hz); 8.05 (1H, d, J=5.0 Hz); 8.24 (1H, 1s, CH=N). 13C NMR (DMSO-d6): δ:2125.96, 132.00, 133.64, 136.96, 137.12.

Workup

  1. customThe solvent was evaporated
  2. customthe residue obtained
  3. washwashed with saturated aqueous sodium bicarbonate (20 mL) and brine
  4. dry with materialThe ethyl acetate layer was dried over MgSO4
  5. customevaporated to a green solid which
  6. customchromatographed (silica, hexane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-aacbc96108194d8791aca191d524aa32
Source dataset
uspto-grants-1995_11
Patent number
US05464831

Reaction notes

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