Triethylamine → HCID 19980941, compound

HRID 974390Notes

Reaction equation

HRID 974390 reaction equation
Cl[Si:2]([CH3:10])([CH3:9])[CH2:3][CH2:4][Si:5](Cl)([CH3:7])[CH3:6].[F:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH2:14][NH2:15].C(N(CC)CC)C.P([O-])(O)(O)=O.[Na+].[Cl-].C([NH+](CC)CC)C>ClCCl>[F:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH2:14][N:15]1[Si:5]([CH3:7])([CH3:6])[CH2:4][CH2:3][Si:2]1([CH3:10])[CH3:9]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 835521,2-Bis(chlorodimethylsilyl)ethaneHCID 27332442,4-DifluorobenzylamineHCID 12698378Triethylazanium chlorideHCID 23672064Monosodium phosphate

Product 1

HCID 19980941HCID 19980941, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

107.6 g (0.05 mol) of 1,2-bis(chlorodimethylsilyl)ethane are introduced into 200 ml of dichloromethane. A solution of 71.6 g (0.50 mol) of 2,4-difluorobenzylamine and 101.2 g (1.0 mol) of triethylamine in 300 ml of dichloromethane are added dropwise at room temperature over the course of 2.5 hours, to give a white suspension. The end of the reaction is checked by gas chromatography. 400 ml of 10% sodium dihydrogen phosphate solution are then added in order to dissolve the precipitated triethylammonium chloride. The organic phase is separated off, dried using magnesium sulfate, filtered and evaporated on a vacuum rotary evaporator. The turbid oil is taken up in 300 ml of petroleum ether, clarified and re-evaporated. 124.7 g of a colourless liquid which is purified by fractional distillation at 125°-127° C. and 15 mbar are obtained. 85.3 g (60% or theory) of pure product are obtained.

Workup

  1. customto give a white suspension
  2. customThe organic phase is separated off
  3. customdried
  4. filtrationfiltered
  5. customevaporated on a vacuum rotary evaporator
  6. customre-evaporated
  7. distillation124.7 g of a colourless liquid which is purified by fractional distillation at 125°-127° C.
  8. custom15 mbar are obtained
  9. custom85.3 g (60% or theory) of pure product are obtained

Sources & evidence

ORD record
ord-8588aa2a0a524025b1cbbe6e141aaaa8
Source dataset
uspto-grants-1991_11
Patent number
US05068371

Reaction notes

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