Methanol → 4-(1,3-Benzothiazol-2-yl)-3-[2-(dimethylamino)ethoxy]aniline

HRID 339505Notes

Reaction equation

HRID 339505 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:11]=1[O:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16].O.O.[Sn](Cl)Cl.CO>CCO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:11]=1[O:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 61436Stannous chloride dihydrateHCID 673122622-[2-(1,3-benzothiazol-2-yl)-5-nitrophenoxy]-N,N-dimethylethanamine

Product 1

HCID 672366574-(1,3-Benzothiazol-2-yl)-3-[2-(dimethylamino)ethoxy]anilineYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared as described in the Nitro Reduction section using 2-[2-(1,3-benzothiazol-2-yl)-5-nitrophenoxy]-N,N-dimethylethanamine (0.073 g, 0.21 mmol) and tin (II) dichloride dihydrate (0.38 g, 1.7 mmol) in EtOH (7 ml) to give the title compound (0.05 g, 75%) as a cream-coloured solid after work-up and flash chromatography (MeOH).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f7d3c7909bc745f19c42e2bf41902b4c
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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