Stannous chloride dihydrate → 2-(4-Amino-3-methoxyphenyl)-6-methoxybenzothiazole

HRID 339504Notes

Reaction equation

HRID 339504 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[S:13][C:14]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.O.O.[Sn](Cl)Cl.CCCCCC.C1COCC1>CCO>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:12]2[S:13][C:14]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 21883165Tetrahydrofuran hexaneHCID 672368252-(3-Methoxy-4-nitrophenyl)-6-methoxybenzothiazole

Product 1

HCID 672383002-(4-Amino-3-methoxyphenyl)-6-methoxybenzothiazoleYield 91.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared as described in the Nitro Reduction section using 2-(3-methoxy-4-nitrophenyl)-6-methoxybenzothiazole (0.5 g, 1.56 mmol) and tin (II) dichloride dihydrate (2.61 g, 11.58 mmol) in EtOH (35 ml) to give the title compound (0.41 g, 91%) as a pale orange solid after work-up and flash chromatography (2:1 Hexane/THF).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-d56b22108b3d4b9e9bdc3c3faaf9660e
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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