Triethylamine → HCID 66606655, compound

HRID 1799350Notes

Reaction equation

HRID 1799350 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.C(N(CC)CC)C.FC(F)(F)S(O[Si:25]([CH3:28])([CH3:27])[CH3:26])(=O)=O>C1(C)C=CC=CC=1>[CH3:26][Si:25]([N:9]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([C:3]#[N:2])=[CH:5][CH:6]=1)[Si:25]([CH3:28])([CH3:27])[CH3:26])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 99422504-(Aminomethyl)benzonitrile hydrochloride

Product 1

HCID 66606655HCID 66606655, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

About 5.20 g of 4-(aminomethyl)benzonitrile hydrochloride, 10.30 g of triethylamine, and 10 ml of toluene were mixed in a round-bottom reaction flask cooled with an ice bath. To this mixture was added, in a dropwise fashion, a solution of 15.1 g of trimethylsilyl trifluoromethanesulfonate in 50 ml of toluene. The resulting mixture was stirred at room temperature for 3 days to give a biphasic mixture. The top layer was transferred to another flask, and the bottom layer was extracted with 40 ml of toluene. The combined toluene solution was evaporated under vacuum. The residue was extracted with 100 ml of hexane, and the hexane layer was evaporated under vacuum, yielding 4-[bis(trimethylsilyl)aminomethyl]benzonitrile (4-BTMSAMBZN) as a white solid (8.12 g, 95% yield). The 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 7.00 (doublet, 2H, aromatic protons), 6.83 (doublet, 2H, aromatic protons), 3.72 (singlet, 2H, CH2 protons), −0.06 (singlet, 18H, Si—CH3 protons). From the 1H NMR data, the structure of the product was determined to be as follows:

Workup

  1. temperaturecooled with an ice bath
  2. additionTo this mixture was added, in a dropwise fashion
  3. customto give a biphasic mixture
  4. customThe top layer was transferred to another flask
  5. extractionthe bottom layer was extracted with 40 ml of toluene
  6. customThe combined toluene solution was evaporated under vacuum
  7. extractionThe residue was extracted with 100 ml of hexane
  8. customthe hexane layer was evaporated under vacuum

Sources & evidence

ORD record
ord-b88c76c827a94e89b0991447a784bb32
Source dataset
uspto-grants-2013_01
Patent number
US08344066B2

Reaction notes

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