Ammonia → 5-Methoxy-2-(6-methoxybenzothiazol-2-yl)phenylamine

HRID 1950097Notes

Reaction equation

HRID 1950097 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]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 61436Stannous chloride dihydrateHCID 2731322-Chloro-6-methoxybenzothiazoleHCID 230873776-Methoxy-2-(4-methoxy-2-nitrophenyl)benzothiazoleHCID 23087474Tributyl(4-methoxy-2-nitrophenyl)tin

Product 1

HCID 230875225-Methoxy-2-(6-methoxybenzothiazol-2-yl)phenylamineYield 75.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

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

  1. filtrationfiltered through celite pad
  2. extractionextracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. customthe solvent was evaporated in vacuo
  5. washthe resulting solid was washed with a hexane-diethyl ether system

Sources & evidence

ORD record
ord-3e6c7f1310e744f3b058b06c0f2284b8
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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