p-Fluoronitrobenzene → 2-(4-nitrophenoxy)-10H-phenothiazine
Reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1>CN(C=O)C>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([O:1][C:2]2[CH:15]=[CH:14][C:13]3[S:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[NH:5][C:4]=3[CH:3]=2)=[CH:24][CH:25]=1)([O-:31])=[O:30]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
1.1 g (5.11 mmol) of 2-hydroxy-10H-phenothiazine (J. Med. Chem. (1992) 35, 716), 1.34 g (9.71 mmol) of K2CO3 and 0.94 g (6.64 mmol) of 4-fluoro-1-nitrobenzene are mixed in 25 ml anhydrous DMF in a flask under argon atmosphere. The reaction mixture is heated at 70° C. for 18 hours. The solvent is then evaporated off under vacuum and the residue is taken up in 50 ml of AcOEt and 50 ml of water. After agitation and decantation, the organic phase is washed with 50 ml of salt water. The organic solution is dried over MgSO4, filtered and concentrated under vacuum. The residue is crystallized from diisopropyl ether. After drying, a yellow solid is obtained with a yield of 83%. Melting point: 210-211° C.
Workup
- customThe solvent is then evaporated off under vacuum
- washAfter agitation and decantation, the organic phase is washed with 50 ml of salt water
- dry with materialThe organic solution is dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe residue is crystallized from diisopropyl ether
- customAfter drying
- customa yellow solid is obtained with a yield of 83%
Sources & evidence
- ORD record
- ord-dc49c717c5b9454f9efa5eaa34c77aaa
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809090B2
Reaction notes
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