p-Toluenesulfonic acid → HCID 135939079, compound

HRID 591851Notes

Reaction equation

HRID 591851 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].C([Si](C)(C)[O:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([CH3:32])[CH:31]=1)[CH:27]=O)(C)(C)C.S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[OH:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]([C:27]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=3[O:13][CH3:14])[N:1]=2)[CH:29]=[C:30]([CH3:32])[CH:31]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium BisulfiteHCID 86662038HCID 86662038, compound

Product 1

HCID 135939079HCID 135939079, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-amino-4,6-dimethoxy-benzamide (0.350 g, 1.78 mmol) in N,N-dimethylacetamide (20 mL) under nitrogen was added 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-benzaldehyde (0.520 g, 1.78 mmol) followed by sodium hydrogensulfite (0.270 g, 2.67 mmol), and p-toluenesulfonic acid (0.033 g, 0.18 mmol). The resulting mixture was heated at 120° C. for 24 hours, then the solvent was concentrated to 5 mL under reduced pressure, and water was added to obtain a precipitate, which was filtered off and washed with Et2O and methylene chloride. The resulting solid was dissolved in hot CH2Cl2/MeOH, and then precipitated by adding Et2O, and purified by preparative thin-layer chromatography (DC-Fertigplatten SIL G-100 UV, 9/1 methylene chloride/MeOH as eluent) to give the title compound as a yellow solid. Yield: 81 mg (13%). MP 106.9-109.1° C. 1H NMR (400 MHz, CDCl3): δ7.86 (s, 1H), 7.41 (d, 2H), 6.82 (s, 1H), 6.57 (s, 1H), 4.15-4.13 (m, 2H), 3.94-3.90 (m, 8H), 2.43 (s, 3H). MS (ES+) m/z: 357.53 (M+1).

Workup

  1. concentrationthe solvent was concentrated to 5 mL under reduced pressure, and water
  2. additionwas added
  3. customto obtain a precipitate, which
  4. filtrationwas filtered off
  5. washwashed with Et2O and methylene chloride
  6. dissolutionThe resulting solid was dissolved in hot CH2Cl2/MeOH
  7. customprecipitated
  8. additionby adding Et2O
  9. custompurified by preparative thin-layer chromatography (DC-Fertigplatten SIL G-100 UV, 9/1 methylene chloride/MeOH as eluent)

Sources & evidence

ORD record
ord-80ba16116b984ebf97b21b5e5d93f21a
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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