Aluminum(III) Chloride → HCID 68229617, compound

HRID 1853867Notes

Reaction equation

HRID 1853867 reaction equation
CS(O[CH2:6][CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]3[C:20]4[CH:33]=[CH:32][S:31][C:21]=4[C:22](=[O:30])[NH:23][C:24]=3[CH:25]=[CH:26][C:27]=2[O:28]C)=[CH:14][CH:13]=1)(=[O:11])=[O:10])(=O)=O.[Cl-:34].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[Cl:34][CH2:6][CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]3[C:20]4[CH:33]=[CH:32][S:31][C:21]=4[C:22](=[O:30])[NH:23][C:24]=3[CH:25]=[CH:26][C:27]=2[OH:28])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 86689549HCID 86689549, compound

Product 1

HCID 68229617HCID 68229617, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenylsulfonamido)ethyl methanesulfonate (250 mg, 0.49 mmol) in anhydrous dichloroethane was added aluminum chloride (330 mg, 2.5 mmol) and the reaction mixture was heated at reflux for 20 h. The reaction was cooled to room temperature, concentrated and quenched with methanol (10 mL). The resulting mixture was allowed to stand at room temperature for 1 h and the resulting precipitate was filtered and dried to afford the desired product (88 mg, 41%) as an off-white solid: 1H NMR (500 MHz, DMSO-d) δ 11.83 (s, 1H), 9.42 (s, 1H), 8.13 (t, J=7.2 Hz, 1H), 7.94 (d, J=5.1 Hz, 2H), 7.74 (d, J=3.3 Hz, 1H), 7.51 (d, J=5.1 Hz, 2H), 7.41 (d, J=5.4 Hz, 1H), 7.18 (d, J=5.4 Hz, 1H), 5.82 (d, J=3.3 Hz, 1H), 3.65 (t, J=3.9 Hz, 2H), 3.22 (q, J=3.6 Hz, 2H); ESI MS m/z 435 [C19H15ClN2O4S2+H]+; HPLC 97.2% (AUC), tR=14.98 min,

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. concentrationconcentrated
  4. customquenched with methanol (10 mL)
  5. filtrationthe resulting precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-dea317fdefbd428390bc101b24bf839b
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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