Acetone → 2-(4'-Nitrophenyl)-6-methylsulfoxy benzothiazole

HRID 1797774Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3C=C(O)[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=[O:21].[K+].[K+].C[S:27](Cl)(=[O:29])=[O:28].[CH3:31][C:32]([CH3:34])=[O:33]>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:13]=[C:15]([CH3:16])[CH:34]=[C:32]([O:33][S:27]([OH:29])(=[O:21])=[O:28])[C:31]=3[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Reactant 4

HCID 180Acetone

HCID 11430Potassium Carbonate

HCID 31297Methanesulfonyl chloride

HCID 108909996-Benzothiazolol, 2-(4-nitrophenyl)-

Product 1

HCID 672640042-(4'-Nitrophenyl)-6-methylsulfoxy benzothiazoleYield 68%

Procedure

To a solution of 2-(4′-nitrophenyl)-6-hydroxy benzothiazole (50 mg, 0.18 mmol) dissolved in acetone (7 mL, anhydrous) was added K2CO3 (100 mg, 0.72 mmol, powdered) and MsCl (200 ul). After stirring for 2 hrs, the reaction mixture was filtered. The filtrate was concentrated and the residue was purified by flash column (silica gel, hexane:ethyl acetate=4:1) to give 2-(4-nitrophenyl)-6-methylsulfoxy benzothiazole (44 mg, 68%) as pale yellow solid. 1HNMR (300 MHz, acetone-d6) δ (ppm): 8.50-8.40(m, 4H), 8.29(d, J=2.3 Hz, 1H), 8.23(d, J=8.9 Hz, 1H), 7.61(dd, J1=2.3 Hz, J2=8.9 Hz, 1H).

Workup

filtrationthe reaction mixture was filtered
concentrationThe filtrate was concentrated
customthe residue was purified by flash column (silica gel, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-81ad8bc3bcc24ed6bc364277b479e4a3
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343457B2

Reaction notes

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