Dibutylamine → HCID 117966115, compound

HRID 56140Notes

Reaction equation

HRID 56140 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.C([O-])([O-])=O.[K+].[K+].[CH2:18]([NH:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>CS(C)=O.O>[CH2:18]([N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[F:1])[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 8148DibutylamineHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 117966115HCID 117966115, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3,4-difluoronitrobenzene (3.18 g, 20 mmol) in DMSO (25 mL) were added K2CO3 (6.08 g, 44 mmol) and di-n-butylamine (2.84 g, 22 mmol) with stirring. The mixture was heated at 90° C. overnight, then cooled to rt, diluted with water (100 mL) and extracted with CH2Cl2 (80 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=10:1) to give the title compound as yellow oil (4.03 g, 75%).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with CH2Cl2 (80 mL×3)
  3. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=10:1)

Sources & evidence

ORD record
ord-edd3c005b7ff421e8b4b6e91a40db2c3
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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