Stannous chloride dihydrate → 2-{4-[2-(3-Aminophenyl)-vinyl]-phenyl}-6-methylbenzothiazole

HRID 339587Notes

Reaction equation

HRID 339587 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][C:20]4[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:21]=4[N:22]=3)=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.O.[Sn](Cl)Cl.C(Cl)Cl.CCOC(C)=O>CCO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][C:20]4[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:21]=4[N:22]=3)=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 21226138Dichloromethane ethylacetateHCID 67238043HCID 67238043, compound

Product 1

HCID 672381502-{4-[2-(3-Aminophenyl)-vinyl]-phenyl}-6-methylbenzothiazoleYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared as described in the Nitro Reduction section using 2-{4-[2-(3-nitrophenyl)-vinyl]-phenyl}-6-methylbenzothiazole (0.12 g, 0.322 mmol) and tin (II) chloride dihydrate (0.58 g, 2.58 mmol) in EtOH (3 ml) to give the title compound (0.078 g, 71%) as a pale yellow solid after work-up and flash chromatography (20:1 DCM/EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e59db627525b4ecebeed42f93bc0be5e
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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