4-Toluenesulfonyl chloride → HCID 57522713, compound

HRID 1403697Notes

Reaction equation

HRID 1403697 reaction equation
CCN([CH2:6][CH3:7])CC.S(Cl)(C1C=CC(C)=CC=1)(=O)=[O:9].[OH:19][CH2:20][CH2:21][N:22]1[C:31]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=3[C:38](=[O:39])[C:30]=2[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:40]>C(Cl)Cl>[C:6]([O:19][CH2:20][CH2:21][N:22]1[C:31]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=3[C:38](=[O:39])[C:30]=2[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:40])(=[O:9])[CH3:7]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 3344746-(2-Hydroxyethyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione

Product 1

HCID 57522713HCID 57522713, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Et3N (34.7 mg, 0.343 mmol), CH3COOAg (57.2 mg, 0.343 mmol), and TsCl (65.4 mg, 0.343 mmol) were added to the solution of 18 (50 mg, 0.172 mmol) in CH2Cl2 (50 mL). The reaction mixture was stirred at room temperature for 16 h, and then washed with sat. NaHCO3 (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated, adsorbed onto SiO2, and purified by flash column chromatography (SiO2), eluting with EtOAc-CHCl3 (2:8) to afford the desired product as a red solid (38.5 mg, 67%): mp 221-224° C. IR (film) 1738, 1693, 1655, and 1506 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.75 (d, J=8.0 Hz, 1 H), 8.37 (d, J=7.9 Hz, 1 H), 7.75 (t, J=5.8 Hz, 2 H), 7.67 (dd, J=1.1 and 5.8 Hz, 1 H), 7.51-7.41 (m, 3 H), 4.84 (t, J=6.2 Hz, 2 H), 4.57 (t, J=6.1 Hz, 2 H), 1.94 (s, 3 H)); probe-EI/CI-MS m/z (rel intensity) 334 (MH+, 100); HRMS (+EI/CI) calcd for M+: 333.1001, found: 333.1005; HPLC purity: 97.3% (MeOH, 100%), 98.0% (MeOH—H2O, 90:10).

Workup

  1. washwashed with sat. NaHCO3 (50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (SiO2)
  6. washeluting with EtOAc-CHCl3 (2:8)

Sources & evidence

ORD record
ord-2407d79a2681456485f242427b64c357
Source dataset
uspto-grants-2014_12
Patent number
US08912213B2

Reaction notes

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