Water → HCID 59313806, compound

HRID 889424Notes

Reaction equation

HRID 889424 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[O:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][NH2:20])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:20][CH2:19][CH2:18][N:15]1[CH2:16][CH2:17][O:12][CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 696992-Bromo-1-fluoro-4-nitrobenzeneHCID 4082852-Morpholinoethylamine

Product 1

HCID 59313806HCID 59313806, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Bromo-1-fluoro-4-nitrobenzene (1.0 g, 4.5 mmol), 2-morpholinoethanamine (0.77 g, 5.9 mmol) and potassium carbonate (1.571 g, 11.4 mmol) in DMSO (5 mL) were stirred at room temperature for 1.5 hours. The mixture was triturated with water, and 2-bromo-N-(2-morpholinoethyl)-4-nitroaniline (1.1 g, 72.8% yield) was collected via filtration. HPLC: Rt=0.61 min. (PHENOMENEX® Luna 5 micron C18 4.6×30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate=5 mL/min., detection at 254 nm). MS (ES): m/z=332.06 [M+H]+.

Sources & evidence

ORD record
ord-8e7dc6e7412f4a87a7018908a64c22ae
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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