HCID 68770101, compound → HCID 59577472, compound

HRID 1947465Notes

Reaction equation

HRID 1947465 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][CH3:21])[C:15]([CH2:22][OH:23])=[CH:14]2>C(Cl)(Cl)Cl.O=[Mn]=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][CH3:21])[C:15]([CH:22]=[O:23])=[CH:14]2

Participants

4

Reactant 1

HCID 68770101HCID 68770101, compound

Product 1

HCID 59577472HCID 59577472, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a solution [5-(benzothiazol-2-yloxy)-1-ethyl-1H-indol-2-yl]-methanol (0.5 g, 1.6 mmol) in CHCl3 (16 mL) was added MnO2 (1.4 g, 16 mmol) and heated (80° C., 3 h). The reaction mixture was cooled (rt), filtered (Celite®) and washed with EtOAc (100 mL). The organic layer was washed with brine (50 mL), dried, filtered and concentrated in vacuo. The resulting residue was recrystallized using EtOAc:hexane (1:3) to provide the title compound as beige solid (0.3 g, 59%). MS (ESI): mass calcd. for C18H14N2O2S, 322.1; m/z found, 323.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.91 (s, 1H), 7.78-7.68 (m, 2H), 7.66 (dd, J=8.0, 0.7, 1H), 7.49 (d, J=9.1, 1H), 7.43-7.34 (m, 2H), 7.30-7.23 (m, 2H), 4.63 (q, J=7.1, 2H), 1.42 (t, J=7.1, 3H).

Workup

  1. temperatureThe reaction mixture was cooled (rt)
  2. filtrationfiltered (Celite®)
  3. washwashed with EtOAc (100 mL)
  4. washThe organic layer was washed with brine (50 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was recrystallized

Sources & evidence

ORD record
ord-80d14dad2f9a4ee0a1dd178e7aa8d993
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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