Ethanol → HCID 563365, compound

HRID 220716Notes

Reaction equation

HRID 220716 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1.[CH3:25]CO>>[CH2:9]([N:8]([CH2:25][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7656DibenzylamineHCID 178418385HCID 178418385, compound

Product 1

HCID 563365HCID 563365, compound

Procedure

H-Benzotriazole-l-methanol (51.0 g, 0.342 mol) was weighed into a round bottom flask and solubilized in EtOH (800 mL). Dibenzylamine (67.5 g, 0.342 mol) was added slowly (over 5 min) to the rapidly stirred solution. Formation of a white precipitate was observed shortly after starting addition. The solution was abandoned to stir for 24 h. At this time the reaction is judged complete by NMR (product fragments on LCMS to show only benzotriazole). The majority of the solvent was removed by rotovap and diethyl ether (1 L) was added to the residue with vigorous stirring. This mixture was filtered, the filtrand washed with ether and dried under vacuum to yield N-(dibenzylaminomethyl)benzotriazole as a fluffy white solid (112 g, quat. yield). 1H NMR (400 MHz, chloroform-d) δ ppm 3.80 (s, 4 H) 5.48 (s, 2 H) 7.21 (d, J=8.34 Hz, 1 H) 7.34-7.43 (m, 11 H) 7.49 (d, 1 H) 8.09 (d, J=7.83 Hz, 1 H).

Workup

  1. additionaddition
  2. customThe majority of the solvent was removed by rotovap and diethyl ether (1 L)
  3. additionwas added to the residue with vigorous stirring
  4. filtrationThis mixture was filtered
  5. washthe filtrand washed with ether
  6. customdried under vacuum
  7. customto yield

Sources & evidence

ORD record
ord-7a8c049a16c94874a505dff988ba13c4
Source dataset
uspto-grants-2012_06
Patent number
US08202990B2

Reaction notes

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