Potassium Carbonate → HCID 86718996, compound

HRID 1746279Notes

Reaction equation

HRID 1746279 reaction equation
[CH2:1]([O:4][CH:5]([CH2:17][O:18][CH2:19][C:20]#[CH:21])[CH2:6][NH:7][C:8]([NH:10][NH:11][C:12](OCC)=[O:13])=[O:9])[C:2]#[CH:3].C(=O)([O-])[O-].[K+].[K+]>CCO>[CH2:1]([O:4][CH:5]([CH2:17][O:18][CH2:19][C:20]#[CH:21])[CH2:6][N:7]1[C:8](=[O:9])[NH:10][NH:11][C:12]1=[O:13])[C:2]#[CH:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86718995HCID 86718995, compound

Product 1

HCID 86718996HCID 86718996, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To ethyl 2-(2,3-bis(prop-2-ynyloxy)propylcarbamoyl)hydrazinecarboxylate (I-13c: 855 mg, 2.88 mmol) in EtOH (14.400 mL) was added potassium carbonate (1590 mg, 11.50 mmol). The mixture was stirred at 65° C. for 16 h. After cooling to room temperature, the mixture was concentrated. HCl 1N was added up to pH-3, and then extracted with AcOEt twice, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (30-100% AcOEt/heptane), and then repurified by silica gel chromatography (0-20% MeOH/CH2Cl2), giving 4-(2,3-bis(prop-2-ynyloxy)propyl)-1,2,4-triazolidine-3,5-dione (1-13d: 238 mg, 33%) as a colorless oil. LC-MS (M+1) 252.1, t=0.72 minute. 1H NMR (400 MHz, CD3CN) δ ppm 2.69 (t, J=2.27 Hz, 1 H) 2.76 (t, J=2.27 Hz, 1 H) 3.47-3.69 (m, 4 H) 3.93-4.04 (m, 1 H) 4.20 (d, J=2.27 Hz, 2 H) 4.22-4.28 (m, 2 H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. additionHCl 1N was added up to pH-3
  4. extractionextracted with AcOEt twice
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (30-100% AcOEt/heptane)
  10. customrepurified by silica gel chromatography (0-20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f20aba8874554ab1a54f5524c035ef5a
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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