4-[4-[(E)-C-methyl-N-prop-2-ynoxycarbonimidoyl]phenyl]-1,2,4-triazolidine-3,5-dione → 4-[4-[(E)-C-methyl-N-prop-2-ynoxycarbonimidoyl]phenyl]-1,2,4-triazole-3,5-dione

HRID 1746265Notes

Reaction equation

HRID 1746265 reaction equation
[CH2:1]([O:4]/[N:5]=[C:6](/[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18](=[O:19])[NH:17][NH:16][C:15]2=[O:20])=[CH:10][CH:9]=1)\[CH3:7])[C:2]#[CH:3]>C(Cl)Cl>[CH2:1]([O:4]/[N:5]=[C:6](/[C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:18](=[O:19])[N:17]=[N:16][C:15]2=[O:20])=[CH:12][CH:13]=1)\[CH3:7])[C:2]#[CH:3]

Participants

3

Reactant 1

HCID 893923294-[4-[(E)-C-methyl-N-prop-2-ynoxycarbonimidoyl]phenyl]-1,2,4-triazolidine-3,5-dione

Product 1

HCID 893923524-[4-[(E)-C-methyl-N-prop-2-ynoxycarbonimidoyl]phenyl]-1,2,4-triazole-3,5-dioneYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (E)-4-(4-(1-(prop-2-ynyloxyimino)ethyl)phenyl)-1,2,4-triazolidine-3,5-dione (I-6a: 46 mg, 0.169 mmol) in CH2Cl2 (1.69 mL) was added SiO2—HNO3 (100 mg). The mixture was stirred at room temperature for 30 minutes, filtered, concentrated in vacuo and dried to give (E)-4-(4-(1-(prop-2-ynyloxyimino)ethyl)phenyl)-3H-1,2,4-triazole-3,5(4H)-dione (24 mg, 53%) as a red solid. 1H NMR (400 MHz, CD3CN) δ ppm 2.31 (s, 3 H) 5.28 (s, 2 H) 7.38 (d, J=7.07 Hz, 1 H) 7.43 (t, J=7.20 Hz, 2 H) 7.46-7.54 (m, 4 H) 7.86-7.94 (m, 2 H). 1H NMR (400 MHz, CD3CN) δ ppm 2.31 (s, 3 H) 2.81 (t, J=2.40 Hz, 1 H) 4.84 (d, J=2.27 Hz, 2 H) 7.53 (d, J=8.84 Hz, 2 H) 7.93 (d, J=8.84 Hz, 2 H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customdried

Sources & evidence

ORD record
ord-bb965cf36466438f8ab93632b5626221
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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