Ammonium Chloride → Aniline

HRID 1783608Notes

Reaction equation

HRID 1783608 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1.[NH4+].[Cl-]>[Zn].CO>[Cl:1][C:2]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1.[C:13]1([NH2:15])[CH:14]=[CH:2][CH:3]=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 534010062-((2-Chloro-4-nitrophenoxy)methyl)thiazole

Product 2

HCID 6115AnilineYield 397.9%HCID 534011103-Chloro-4-[(1,3-thiazol-2-yl)methoxy]aniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

3-Chloro-4-(thiazol-2-ylmethoxy)-phenylamine is prepared by added Zn dust (55.9 g, 856 mmol) to a mixture of 2-(2-chloro-4-nitro-phenoxymethyl)-thiazole (47.0 g, 190 mmol) in 5:1 MeOH:saturated aqueous NH4Cl solution (600 ml). After 2 h, the reaction mixture is filtered, and the filtrate concentrated. The resulting solid is triturated with water to give 3-chloro-4 thiazol-2-ylmethoxy)-phenylamine (35.2 g, 85%).

Workup

  1. filtrationthe reaction mixture is filtered
  2. concentrationthe filtrate concentrated
  3. customThe resulting solid is triturated with water

Sources & evidence

ORD record
ord-fdaaf12318204a90ac517e6ccd5a3a9a
Source dataset
uspto-grants-2009_03
Patent number
US07501427B2

Reaction notes

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