Diethylamine → HCID 21707796, compound

HRID 2379374Notes

Reaction equation

HRID 2379374 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[CH:5]=[O:6].[CH2:11]([NH:13][CH2:14][CH3:15])[CH3:12].FC1C(F)=C(C=CC=1)C=O>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[CH:8][C:9]=1[N:13]([CH2:14][CH3:15])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 1376642,3-DifluorobenzaldehydeHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 21707796HCID 21707796, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 250 mL round bottom flask equipped with stirbar, condenser and nitrogen inlet was placed 3,4-difluorobenzaldehyde (25.0 g, 176 mmol), dimethylsulfoxide (50 mL) and diethylamine (38.6 g, 528 mmol). The resulting solution was boiled gently for 6 hr at which time thin layer chromatography indicated all the difluorobenzaldehyde was consumed. The solution was cooled and transferred to a separatory funnel with ethyl acetate and water. The phases were separated, the organic phase washed well with water, dried (MgSO4) and filtered through a short pad of silica gel. Silica gel (50 g) was added to the filtrate and the mixture concentrated to dryness. This material was placed at the top of a column of silica gel and eluded with a gradient of ethylacetate in hexane (0→4%). Concentration of the pure fractions by rotary evaporation afforded a light brown oil (31.97 g, 92%) of sufficient purity for subsequent transformations: IR (CCl4)1695 cm-1 ; 1H NMR (CDCl3)δ9.70 (s, 1H), 7.41-7.50 (m, 2H), 6.78 (t, J= 8Hz, 1H), 3.39 (q, J=7 Hz, 4H), 1.20 (t, J=7 Hz, 6H); 13C NMR (CDCl3) ppm 189.048, 151.901 (d, J=244 Hz), 142.844 (d, J=8 Hz), 127.880. 126.244 (d, 6 Hz), 116.433 (d, J=23Hz), 115.316 (d, 5 Hz), 45.845 (d, J=6Hz), 12.858 d,J=1 Hz).

Workup

  1. customIn a 250 mL round bottom flask equipped with stirbar, condenser and nitrogen inlet
  2. customwas consumed
  3. temperatureThe solution was cooled
  4. customtransferred to a separatory funnel with ethyl acetate and water
  5. customThe phases were separated
  6. washthe organic phase washed well with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered through a short pad of silica gel
  9. additionSilica gel (50 g) was added to the filtrate
  10. concentrationthe mixture concentrated to dryness
  11. customConcentration of the pure fractions by rotary evaporation

Sources & evidence

ORD record
ord-2e7c472763f049d08559c21be75f3e5c
Source dataset
uspto-grants-1994_11
Patent number
US05361148

Reaction notes

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