Hydrochloric Acid → HCID 86718990, compound

HRID 1746269Notes

Reaction equation

HRID 1746269 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]([NH:17][C:18]([NH:20][NH:21][C:22]([O:24]CC)=O)=[O:19])=[CH:13][CH:12]=1)[C:2]#[CH:3].C([O-])([O-])=O.[K+].[K+].Cl.O1CCOCC1>CO>[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[C:18](=[O:19])[NH:20][NH:21][C:22]2=[O:24])=[CH:15][CH:16]=1)[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 86718989HCID 86718989, compound

Product 1

HCID 86718990HCID 86718990, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To ethyl 2-(4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)phenylcarbamoyl)-hydrazinecarboxylate (1.31 g, 3.59 mmol) in methanol (17.93 mL) was added K2CO3 (1.239 g, 8.96 mmol). The mixture was stirred at 55° C. for 30 minutes. After cooling to room temperature, 4N HCl in dioxane (3.59 mL, 14.34 mmol) was added. The precipitate was filtered, and the filtrate was concentrated in vacuo. The residue was then purified by silica gel chromatography (40-100% ethyl acetate/heptane) giving 4-(4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)phenyl)-1,2,4-triazolidine-3,5-dione (I-7d: 318 mg, 28%) as a white oily solid. LC-MS (M+1) 320.0, t=0.73 minute. 1H NMR (400 MHz, CDCl3) δ ppm 2.48 (t, J=2.15 Hz, 1 H) 3.68-3.83 (m, 4 H) 3.83-3.97 (m, 2 H) 4.11-4.32 (m, 4 H) 7.04 (d, J=8.84 Hz, 2 H) 7.36 (d, J=8.84 Hz, 2 H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitate was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was then purified by silica gel chromatography (40-100% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-6f10d873e23b4673a0a6fb71bc1ac195
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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