HCID 86718990, compound → HCID 86718991, compound

HRID 1746270Notes

Reaction equation

HRID 1746270 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21](=[O:22])[NH:20][NH:19][C:18]2=[O:23])=[CH:13][CH:12]=1)[C:2]#[CH:3]>C(Cl)Cl>[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:18](=[O:23])[N:19]=[N:20][C:21]2=[O:22])=[CH:13][CH:12]=1)[C:2]#[CH:3]

Participants

3

Reactant 1

HCID 86718990HCID 86718990, compound

Product 1

HCID 86718991HCID 86718991, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-(4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)phenyl)-1,2,4-triazolidine-3,5-dione (I-7d: 153 mg, 0.479 mmol) in CH2Cl2 (4.792 mL) was added SiO2-HNO3 (300 mg). The mixture was stirred at room temperature for 15 minutes, then filtered, concentrated in vacuo and dried giving 4-(4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)phenyl)-3H-1,2,4-triazole-3,5(4H)-dione (112 mg, 74%) as a red oil. 1H NMR (400 MHz, CD3CN) δ ppm 2.60 (t, J=2.40 Hz, 1 H) 3.44-3.62 (m, 4 H) 3.68-3.75 (m, 2 H) 4.02-4.12 (m, 4 H) 7.02 (d, J=9.09 Hz, 2 H) 7.23 (d, J=8.84 Hz, 2 H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customdried

Sources & evidence

ORD record
ord-0476696b161d49bb9faf4881cace4ac9
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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