Ethyl Acetate → 4-(1,3-Benzothiazol-2-yl)-3-[2-{2-(2-methoxyethoxy)ethoxy}ethoxy]aniline

HRID 339506Notes

Reaction equation

HRID 339506 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:13]=1[C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.O.O.[Sn](Cl)Cl.CCOC(C)=O>CCO>[S:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[C:13]1[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:12]=1[O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 672375212-[2-{2-(2-(2-Methoxyethoxy)ethoxy)ethoxy}-4-nitrophenyl]-1,3-benzothiazole

Product 1

HCID 672371794-(1,3-Benzothiazol-2-yl)-3-[2-{2-(2-methoxyethoxy)ethoxy}ethoxy]anilineYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared as described in the Nitro Reduction section using 2-[2-{2-(2-(2-methoxyethoxy)ethoxy)ethoxy}-4-nitrophenyl]-1,3-benzothiazole (0.15 g, 0.36 mmol) and tin (II) dichloride dihydrate (0.65 g, 2.87 mmol) in EtOH (12 to give the title compound (0.13 g, 92%) as a viscous, yellow oil after work-up and flash chromatography (EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2cd4528cfe24485ba3f1531b1734826e
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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