2-Fluoroaniline → HCID 18929261, compound

HRID 1599844Notes

Reaction equation

HRID 1599844 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:8][CH:7]=1)=[O:4].[F:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20]>CN(C=O)C>[F:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 18929230HCID 18929230, compound

Product 1

HCID 18929261HCID 18929261, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-((bromoacetyl)amino)-1-butoxybenzene (1.0 g, 3.5 mmol) and 2-fluoroaniline (1.0 g, 0.87 mL, 8.8 mmol) in anhydrous DMF (30 mL) was heated to 90°-100° C. overnight with stirring under N2. The solution was cooled, poured into 500 mL of ice-water, and then extracted with CH2Cl2 (3×50 mL). The layers were separated and the organic layer was dried (MgSO4), filtered and then concentrated to an oily residue. Purification by chromatography, eluting with hexane-ethyl acetate (2:1), afforded 0.50 g (45%) of the title compound, mp 92°-94° C.: 1H NMR (DMSO-d6) δ9.86 (s, 1H), 7.47 (d, J=8.8, 2H), 7.04 (ddd, J=9.6, J=8.0, J=1.2, 1H), 6.94 (dt, J=8.0, J=0.8, 1H), 6.86 (d, J=9.6, 2H), 6.63-6.58 (m, 2H), 5.73 (bt, J=2.0, 1H), 3.90 (q, J=6.0, 2H), 3.46 (s, 2H), 1.68-1.64 (m, 2H), 1.44-1.40 (m, 2H), 0.91 (t, J=5.6, 3H); 13C NMR (DMSO-d6) δ168.24, 154.69, 150.90 (d, J=236), 136.46, 131.79, 124.73 (d, J=3.5), 120.79, 116.22 (d, J=6.3), 114.48 (d, J=5.6), 114.33 (d, J=126), 112.11 (d, J=3.6), 67.21, 46.57, 30.75, 18.70, 13.66; MS (El, m/z) 316 (M+).

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with CH2Cl2 (3×50 mL)
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to an oily residue
  7. customPurification by chromatography
  8. washeluting with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-4b8f46d70ed84a84940167e7328b6add
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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