p-Fluoronitrobenzene → 4-[(Pyridin-2-yl)sulfanyl]aniline

HRID 2222310Notes

Reaction equation

[SH:1][C:2]1SC=[C:5]([C:7]2C=CC=[CH:9][CH:8]=2)[N:6]=1.F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[N:6]1[CH:5]=[CH:7][CH:8]=[CH:9][C:2]=1[S:1][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 65 °C

Procedure

4-(2-(4-Phenyl)thiazolyl)thio-1-nitrobenzene: A solution of 2-mercapto-4-phenylthiazole (4.0 g, 20.7 mmoles) in DMF (40 mL) was treated with 1-fluoro-4-nitrobenzene (2.3 mL, 21.7 mmoles) followed by K2CO3 (3.18 g, 23 mmol), and the mixture was heated at approximately 65° C. overnight. The reaction mixture was then diluted with EtOAc (100 mL), sequentially washed with water (100 mL) and a saturated NaCl solution (100 mL), dried (MgSO4) and concentrated under reduced pressure. The solid residue was triturated with a Et2O/hexane solution to afford the desired product (6.1 g): TLC (25% EtOAc/75% hexane) Rf 0.49; 1H-NMR (CDCl3) δ 7.35-7.47 (m, 3H), 7.58-7.63 (m, 3H), 7.90 (d, J=6.9 Hz, 2H), 8.19 (d, J=9.0 Hz, 2H).

Workup

washsequentially washed with water (100 mL)
dry with materiala saturated NaCl solution (100 mL), dried (MgSO4)
concentrationconcentrated under reduced pressure
customThe solid residue was triturated with a Et2O/hexane solution

Sources & evidence

ORD record: ord-58022203ee6844c799f8d90de143410e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371763B2

Reaction notes

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