Ammonia → 5-Methoxy-2-(6-methoxybenzothiazol-2-yl)phenylamine
Reaction equation
ClC1SC2C=C(OC)C=CC=2N=1.C([Sn](CCCC)(CCCC)C1C=CC(OC)=CC=1[N+]([O-])=O)CCC.[CH3:37][O:38][C:39]1[CH:58]=[CH:57][C:42]2[N:43]=[C:44]([C:46]3[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][C:47]=3[N+:54]([O-])=O)[S:45][C:41]=2[CH:40]=1.O.O.[Sn](Cl)Cl.N>C(O)C.Cl>[CH3:53][O:52][C:49]1[CH:50]=[CH:51][C:46]([C:44]2[S:45][C:41]3[CH:40]=[C:39]([O:38][CH3:37])[CH:58]=[CH:57][C:42]=3[N:43]=2)=[C:47]([NH2:54])[CH:48]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Synthesized from 2-chloro-6-methoxybenzothiazole and tributyl(4-methoxy-2-nitrophenyl)tin according to an analogous synthetic method to Preparation Example 77, to a suspension of the resulting 6-methoxy-2-(4-methoxy-2-nitrophenyl)benzothiazole (695 mg) in ethanol (10 ml) and concentrated hydrochloric acid (2 ml) was added tin(II) chloride dihydrate (1.3 g), and the solution was stirred for 7 hours at room temperature. The solution was neutralized with ammonia solution on an ice bath, then filtered through celite pad, extracted with ethyl acetate, then sequentially washed with water and brine, the solvent was evaporated in vacuo, the resulting solid was washed with a hexane-diethyl ether system to provide the title compound (475 mg).
Workup
- filtrationfiltered through celite pad
- extractionextracted with ethyl acetate
- washsequentially washed with water and brine
- customthe solvent was evaporated in vacuo
- washthe resulting solid was washed with a hexane-diethyl ether system
Sources & evidence
- ORD record
- ord-f85a7524f0cc45b089eaff2ca5e047b0
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612114B2
Reaction notes
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