Water → HCID 59313895, compound

HRID 889427Notes

Reaction equation

HRID 889427 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][OH:21])[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][O:21][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 611632-MorpholinoethanolHCID 27746544-Fluoro-3-nitrobenzonitrile

Product 1

HCID 59313895HCID 59313895, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Fluoro-3-nitrobenzonitrile (0.5 g, 3.0 mmol), 2-morpholinoethanol (0.37 mL, 3.0 mmol), and potassium carbonate (0.42 g, 3.0 mmol) in DMSO (2 mL) were heated at 50° C. for 16 hours. Water (10 mL) was added to the reaction mixture, and the solid was collected via filtration. The solid was washed with water (3×2 mL) to afford Intermediate 27A (422 mg, 50.6% yield) as a tan solid. HPLC: Rt=0.78 min. (PHENOMENEX® S5 4.6×30 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min. gradient, flow rate=5 mL/min., detection at 254 nm). MS (ES): m/z=278.16 [M+H]+.

Workup

  1. filtrationthe solid was collected via filtration
  2. washThe solid was washed with water (3×2 mL)

Sources & evidence

ORD record
ord-76f0ec85904245dcb6b6ab3a8173e83a
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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