Diisopropylethylamine → Methanesulfonic acid 2-[6-(benzothiazol-2-yloxy)-benzofuran-3-yl]-ethyl ester

HRID 1947478Notes

Reaction equation

HRID 1947478 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:22]=[CH:21][C:14]2[C:15]([CH2:18][CH2:19][OH:20])=[CH:16][O:17][C:13]=2[CH:12]=1.CCN(C(C)C)C(C)C.[O:32](S(C)(=O)=O)[S:33]([CH3:36])(=O)=[O:34]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[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:22]=[CH:21][C:14]2[C:15]([CH2:18][CH2:19][O:20][S:33]([CH3:36])(=[O:34])=[O:32])=[CH:16][O:17][C:13]=2[CH:12]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 667868102-[6-(Benzothiazol-2-yloxy)-benzofuran-3-yl]-ethanol

Product 1

HCID 59577553Methanesulfonic acid 2-[6-(benzothiazol-2-yloxy)-benzofuran-3-yl]-ethyl esterYield 105.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[6-(benzothiazol-2-yloxy)-benzofuran-3-yl]-ethanol (0.32 g, 1.0 mmol) in DCM (15 mL) was added 4-dimethylaminopyridine (13 mg, 0.10 mmol), DIEA (0.22 mL, 1.2 mmol) and Ms2O (0.22 g, 1.2 mmol) and the resulting solution was stirred (rt, 15 min). The reaction mixture was diluted with DCM (40 mL). The organic layer was washed with saturated NH4Cl (2×50 mL), brine (2×50 mL), dried, filtered and concentrated in vacuo to provide the title compound as a clear oil (0.41 g, 100%). MS (ESI): mass calcd. for C18H15NO5S2, 389.5; m/z found, 390.1 [M+H]+.

Workup

  1. washThe organic layer was washed with saturated NH4Cl (2×50 mL), brine (2×50 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18ab308575fc461a9a3e500af9ba9a24
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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