p-Toluenesulfonic acid monohydrate → HCID 91002123, compound

HRID 272760Notes

Reaction equation

HRID 272760 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:14]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:15]=1[C:16](OC)=[O:17].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:24][C:22]1[CH:21]=[CH:20][C:15]2[C:16](=[O:17])[NH:1][C:2]3[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:4][C:3]=3[NH:13][C:14]=2[CH:23]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 69217724HCID 69217724, compound

Product 1

HCID 91002123HCID 91002123, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of Example 695C (0.3 g, 0.91 mmol) and TsOH.H2O (0.35 g, 1.82 mmol) in toluene (50 mL) was heated to reflux for 20 hours using a Dean-Stark trap to remove water. The reaction was cooled to room temperature, concentrated under vacuum, diluted with ethyl acetate, washed with saturated NaHCO3 and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate to provide 0.21 g (81%) of the desired product. MS (DCI) m/e 317 (M+H)+, 334 (M+NH4)+; 1H NMR (500 MHz, DMSO-d6) δ 9.88 (s, 1H), 8.03 (s, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.06 (d, J=2.2 Hz, 1H), 6.91-6.93 (m, 2H), 6.86-6.87 (m, 2H), 3.60 (s, 3H), 3.54 (s, 2H).

Workup

  1. temperatureto reflux for 20 hours
  2. customto remove water
  3. concentrationconcentrated under vacuum
  4. additiondiluted with ethyl acetate
  5. washwashed with saturated NaHCO3 and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-ba008b8e3c2c4dacbe7d39c8a498e369
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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