Benzocaine → HCID 67048229, compound

HRID 1478933Notes

Reaction equation

HRID 1478933 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)S(O[Si:26]([CH3:29])([CH3:28])[CH3:27])(=O)=O>C1(C)C=CC=CC=1>[CH3:27][Si:26]([N:1]([Si:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 65367Trimethylsilyl triflate

Product 1

HCID 67048229HCID 67048229, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

About 9.24 g of ethyl 4-aminobenzoate, 14.88 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 32.68 g of trimethylsilyl trifluoromethanesulfonate in 50 ml of toluene. The resulting mixture was heated to reflux for 8 hours 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 ethyl 4-[bis(trimethylsilyl)amino]benzoate (4-BTMSAEBz) as a yellow oil (16.04 g, 93% yield). The 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 8.07 (doublet, 2H, aromatic protons), 6.76 (doublet, 2H, aromatic protons), 4.12 (quartet, 2H, CH2 protons), 1.00 (triplet, 3H, CH3 protons), 0.02 (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. temperatureThe resulting mixture was heated
  4. temperatureto reflux for 8 hours
  5. customto give a biphasic mixture
  6. customThe top layer was transferred to another flask
  7. extractionthe bottom layer was extracted with 40 ml of toluene
  8. customThe combined toluene solution was evaporated under vacuum
  9. extractionThe residue was extracted with 100 ml of hexane
  10. customthe hexane layer was evaporated under vacuum

Sources & evidence

ORD record
ord-c0623e120aaa40398019f7277a86a796
Source dataset
uspto-grants-2016_08
Patent number
US09403919B2

Reaction notes

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