Triethylamine → 2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

HRID 1397969Notes

Reaction equation

HRID 1397969 reaction equation
N(CCN)=[N+]=[N-].C(N(CC)CC)C.[CH:14]1[C:19](N=C=S)=[CH:18][C:17]2[C:23]([O:25][C:26]3([C:36]4[CH:37]=[CH:38][C:39]([OH:41])=[CH:40][C:35]=4[O:34][C:28]4[CH:29]=[C:30]([OH:33])[CH:31]=[CH:32][C:27]3=4)[C:16]=2[CH:15]=1)=[O:24]>ClCCl>[CH:14]1[CH:19]=[CH:18][C:17]([C:23]([OH:25])=[O:24])=[C:16]([C:26]2[C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][C:28]=3[O:34][C:35]3[C:36]=2[CH:37]=[CH:38][C:39]([CH:40]=3)=[O:41])[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18730Fluorescein 5-isothiocyanateHCID 55649Ethylamine, 2-azido-

Product 1

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon atmosphere, to a solution of 2-azidoethylamine (16) (˜50%, 1H NMR) (synthesized by the method described in Non-Patent Document: R. Srinivasan, L. P. Tan, H. Wu, P. Yang, K. A. Kalesh, S. Q. Yao, Org. Biomol. Chem. 2009, 7, 1821-1828) (200 mg, ˜1.16 mmol) in dichloromethane (5 mL) were successively added triethylamine (70.0 μL, 502 μmol) and fluorescein isothiocyanate isomer I (FITC, 17, commercial product) (90%, HPLC) (100 mg, 231 μmol) at room temperature. After stirring for 21 hours at the same temperature, the reaction solution was concentrated under reduced pressure using an evaporator. The residue was purified by flash column chromatography (silica-gel 30 g, dichloromethane/methanol=9/1) to give 1-(2-azidoethyl)-3-(5-fluoresceinyl)thiourea (18) (109 mg, 229 μmol, 99.2%) as an orange solid.

Workup

  1. customat room temperature
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customan evaporator
  4. customThe residue was purified by flash column chromatography (silica-gel 30 g, dichloromethane/methanol=9/1)

Sources & evidence

ORD record
ord-bf839249b15b4dbf9ed2273a105c1b5b
Source dataset
uspto-grants-2014_12
Patent number
US08901312B2

Reaction notes

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