Thionyl Chloride → HCID 59577775, compound

HRID 1947474Notes

Reaction equation

HRID 1947474 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]=[CH:13][C:14]2[O:18][C:17]([CH2:19]O)=[CH:16][C:15]=2[CH:21]=1.CCN(C(C)C)C(C)C.S(Cl)([Cl:33])=O>C(Cl)Cl>[Cl:33][CH2:19][C:17]1[O:18][C:14]2[CH:13]=[CH:12][C:11]([O:10][C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[CH:21][C:15]=2[CH:16]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 59577402HCID 59577402, compound

Product 1

HCID 59577775HCID 59577775, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-(benzothiazol-2-yloxy)-benzofuran-2-yl]-methanol (55 mg, 0.19 mmol) and DIEA (0.042 mL, 34 mg, 0.24 mmol) in DCM (0.8 mL) was added thionyl chloride (0.017 mL, 26 mg, 0.22 mmol) and the resulting mixture was stirred (rt, 2 h). The reaction mixture was concentrated under a stream of nitrogen to afford the title compound (50 mg, 100%). MS (ESI): mass calcd for C16H10NO2SCl, 315.0; m/z found 316.1 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-f92102cff7d94e99836dd01f0f9c08ae
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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