Water → 2-chloro-N-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)-4-nitroaniline

HRID 56222

Reaction equation

Cl.[CH3:2][C:3]([NH2:16])([CH3:15])[CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1.[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1F.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1[NH:16][C:3]([CH3:2])([CH3:15])[CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-methyl-1-(naphthalen-2-yl)propan-2-amine hydrochloride (5.9 g, 25.0 mmol), 3-chloro-4-fluoro-1-nitrobenzene (5.27 g, 30.0 mmol) and K2CO3 (6.9 g, 50.0 mmol) in DMSO (50 mL) was stirred at 140° C. overnight. The mixture was cooled to rt and poured into 150 mL of water. The mixture was then extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/DCM (V/V)=10:1) to give the title compound as yellow foam (3.78 g, 43%).

Workup

temperatureThe mixture was cooled to rt
extractionThe mixture was then extracted with EtOAc (50 mL×3)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/DCM (V/V)=10:1)

Sources & evidence

ORD record: ord-3950c11c8b84445db2e60821f7773461
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Linked notes

Loading…