Sodium Carbonate → HCID 57429816, compound

HRID 659138Notes

Reaction equation

HRID 659138 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]([CH:11]([CH3:13])[CH3:12])[C:9]#[CH:10])=[O:6].C(=O)([O-])[O-].[Na+].[Na+]>O>[NH3:4].[CH3:12][CH:11]([CH3:13])[CH:8]([NH:7][C:5]1[O:6][CH2:2][CH2:3][N:4]=1)[C:9]#[CH:10]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 57429815HCID 57429815, compound2×

Product 2

HCID 222AmmoniaYield 5%HCID 57429816HCID 57429816, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 169 mg of 1-(2-chloroethyl)-3-(4-methylpent-1-yn-3-yl)urea (Formula 24) in 10 mL of water was heated at 100° C. for 2.5 hours. The reaction mixture was cooled to room temperature. Then, a saturated solution of sodium carbonate was added to adjust the pH of the solution to greater than 8. The mixture was extracted with ethyl acetate. The combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (5% 7N NH3 in MeOH/CH2Cl2) gave 60 mg of N-(4-methylpent-1-yn-3-yl)-4,5-dihydrooxazol-2-amine (Formula 25) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.01 (m, 6H), 1.95-2.02 (m, 1H), 2.28-2.29 (m, 1H), 3.76-3.83 (m, 2H), 4.24-4.32 (m, 3H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe combined ethyl acetate was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-41adcc48c47b4b54879ceb53c52cd408
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Reaction notes

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