Dimethylformamide → HCID 87442358, compound

HRID 1176169Notes

Reaction equation

HRID 1176169 reaction equation
[CH2:1]([N:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CN([CH:23]=[O:24])C.O=P(Cl)(Cl)Cl.CC([O-])=O.[Na+]>ClCCCl>[CH2:14]([N:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[CH:23]=[O:24])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 138236N,N-DihexylanilineHCID 517045Sodium Acetate

Product 1

HCID 87442358HCID 87442358, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N,N-dihexylaniline (12.02 g, 4.60×10−2 mol) in anhydrous 1,2-dichloroethane (200 ml) at room temperature were successively added anhydrous DMF (3.60 ml, 4.65×10−2 mol) and POCl3 (5.20 ml, 5.58×10−2 mol), and the mixture was refluxed for 5.5 h. After cooling, 2M aqueous NaOAc solution (200 ml) was added and the reaction mixture was stirred overnight. The product was extracted three times with CHCl3 and the combined organic layers were dried over Na2SO4. The residue was chromatographed on silica gel with 1:1 hexane:CHCl3 as the eluent. Yield=10.793 g (81% based on 12.02 g of N,N-dihexylaniline). 1H NMR (250 MHz, CDCl3): δ 9.69 (s, 1H, —CHO), 7.70 (dd, 2H, J=8.9 Hz, Ph), 6.63 (d, 2H, J=9.0 Hz, Ph), 3.34 (t, 4H, J=7.8 Hz, —NCH2—), 1.48-1.70 (m, 4H, —NCH2CH2—), 1.19-1.41 (m, 12H, —CH2—), 0.91 (t, 6H, J=6.6 Hz, —CH3). CI MS m/z: 290.247 ((M+H)+) (calcd 290.248).

Workup

  1. customat room temperature
  2. temperaturethe mixture was refluxed for 5.5 h
  3. temperatureAfter cooling
  4. extractionThe product was extracted three times with CHCl3
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. customThe residue was chromatographed on silica gel with 1:1 hexane

Sources & evidence

ORD record
ord-a444cd2c4d9c4ca1a27f2087435fc037
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

Loading…