Stannous chloride dihydrate → 4-(1,3-Benzothiazol-2-yl)-3-methoxyaniline

HRID 339496Notes

Reaction equation

HRID 339496 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1.O.O.[Sn](Cl)Cl.CCCCCC.C1COCC1>CCO>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([C:12]2[S:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 21883165Tetrahydrofuran hexaneHCID 672372802-(2-Methoxy-4-nitrophenyl)benzothiazole

Product 1

HCID 672368764-(1,3-Benzothiazol-2-yl)-3-methoxyanilineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared as described in the Nitro Reduction section using 2-(2-methoxy-4-nitrophenyl)benzothiazole (0.1 g, 0.35 mmol) and tin (II) dichloride dihydrate (0.63 g, 2.8 mmol) in EtOH (12 ml) to give the title compound (0.086 g, 96%) as a pale orange solid after work-up and flash chromatography (2:1 Hexane/THF).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-dbbd9d4103324bac9695dc404b6b5456
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

Loading…