Potassium Carbonate → 2-(5-Nitro-2-pyridinylthio)ethyl-3-chlorobenzoate

HRID 731765Notes

Reaction equation

[SH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Br[CH2:12][CH2:13][O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:12][CH2:13][O:14][C:15](=[O:23])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 55 °C

Procedure

A heterogeneous mixture of 2-mercapto-5-nitropyridine (4) (46 mg, 0.29 mmol), 2-bromoethyl-3-chlorobenzoate (3) (77 mg, 0.29 mmol), and K2CO3 (0.160 g, 1.1 mmol) in acetone (1 mL) was stirred at 55° C. for 5 h. The cooled reaction mixture was filtered through Celite®, concentrated, and then purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)thio]ethyl-3-chlorobenzoate (5) as a white solid. 1H NMR (CDCl3): δ 9.22 (d, J=1.8 Hz, 1H), 8.24 (dd, J=2.4 and 9.0 Hz, 1H), 7.95-7.91 (m, 1H), 7.90 (t, J=0.9 Hz, 1H), 7.56-7.51 (m, 1H), 7.39 (d, J=8.1 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 4.61 (t, J=6.6 Hz, 2H), 3.68 (t, J=6.6 Hz, 2H)

Workup

customThe cooled reaction mixture
filtrationwas filtered through Celite®
concentrationconcentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-a51decfe2ead4b24b96f6d50b1c4bdc9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585883B2

Reaction notes

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