Ammonium Chloride → 4-{[2-(Dimethylamino)ethyl]sulfanyl}aniline

HRID 2236689Notes

Reaction equation

[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.[Cl-].[NH4+]>C(O)C.O1CCCC1.[Fe]>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N,N-dimethyl-N-{2-[(4-nitrophenyl)thio]ethyl}amine (0.58 g, 3.0 mmol) in ethanol (45 mL), tetrahydrofuran (23 mL), and saturated aqueous ammonium chloride solution is added iron powder (1.1 g, 6.4 mmol). The mixture is heated in a 100° C. oil bath for one hour. While still hot, the reaction mixture is filtered through a pad of diatomaceous earth. The concentrated filtrate is partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material is purified by reverse-phase high performance liquid chromatography to give 4-(2-dimethylamino-ethylsulfanyl)-phenylamine.

Workup

filtrationWhile still hot, the reaction mixture is filtered through a pad of diatomaceous earth
customThe concentrated filtrate is partitioned between ethyl acetate and saturated aqueous sodium chloride solution
dry with materialThe organic phase is dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude material is purified by reverse-phase high performance liquid chromatography

Sources & evidence

ORD record: ord-b8f291aa292b45118c3b7630413dd9cf
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713994B2

Reaction notes

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