Ethanethiol → HCID 58913126, compound

HRID 1296687Notes

Reaction equation

HRID 1296687 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:32]=[CH:31][C:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:20]C)=[CH:17][CH:18]=3)[O:13][C:12](=[O:22])[C:11]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])=[CH:7][CH:6]=1.[Al+3].[Cl-].[Cl-].[Cl-].CCS.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:32]=[CH:31][C:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[O:13][C:12](=[O:22])[C:11]=2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 589130934-(4-(2-Bromoethoxy)-benzyl)-3-(2,4-dichlorophenyl)-7-methoxy-chromen-2-one

Product 1

HCID 58913126HCID 58913126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-(4-(2-bromoethoxy)-benzyl)-3-(2,4-dichlorophenyl)-7-methoxy-chromen-2-one (4.0 g, 7.49 mmol), AlCl3 (5.89 g, 44.2 mmol), and EtSH (2.77 mL, 37.4 mmol) in CH2Cl2 (200 mL) was stirred at room temperature for 2.5 h. The mixture was slowly poured into CH2Cl2/sat. aq NaHCO3. The resultant layers were separated, and the aqueous phase was further extracted with CH2Cl2 (3×). The aqueous layer was raised to pH 10 with aqueous 2M NaOH and extracted with AcOEt (3×). Each organic layer was washed with brine and dried (MgSO4), and the combined organic phases were concentrated in vacuo. The resultant residue was purified using flash chromatography (250 g silica gel, 95:5→9:1 CH2Cl2:AcOEt) to afford the title compound, which was isolated as an off-white solid (3.454 g, 89%). 1H NMR (300 MHz, CDCl3) δ 7.50 (d, J=2.0 Hz, 1H), 7.42 (d, J=8.8 Hz, 1H), 7.25 (dd, J=2.0, 8.0 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 6.99 (d, J=2.0 Hz, 1H), 6.94 (d, J=8.5 Hz, 2H), 6.78 (d, J=8.5 Hz, 2H), 6.73 (dd, J=2.0, 8.8 Hz, 1H), 6.61–6.49 (br signal, 1H), 4.23 (t, J=6.0 Hz, 2H), 4.04 (d, J=15.5 Hz, 1H), 3.78 (d, J=15.5 Hz, 1H), 3.61 (t, J=6.0 Hz, 2H); MS (ESI) m/z 516.9 (M−H)−; HPLC tR 7.41 min.

Workup

  1. customThe resultant layers were separated
  2. extractionthe aqueous phase was further extracted with CH2Cl2 (3×)
  3. temperatureThe aqueous layer was raised to pH 10 with aqueous 2M NaOH
  4. extractionextracted with AcOEt (3×)
  5. washEach organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationthe combined organic phases were concentrated in vacuo
  8. customThe resultant residue was purified

Sources & evidence

ORD record
ord-cef1754574b64351a4b5aa5e9dfd44fc
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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