Sodium Carbonate → HCID 44480000, compound

HRID 659141Notes

Reaction equation

HRID 659141 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:9]#[CH:10])=[O:6].C(=O)([O-])[O-].[Na+].[Na+]>O>[NH3:4].[O:6]1[CH2:2][CH2:3][N:4]=[C:5]1[NH:7][CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:9]#[CH:10]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 57429817HCID 57429817, compound2×

Product 2

HCID 222AmmoniaYield 3%HCID 44480000HCID 44480000, compoundYield 146%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 136 mg of 1-(2-chloro-ethyl)-3-(1-phenyl-prop-2-ynyl)-urea (Formula 29) in 5 mL of water was heated at 100° C. for 2.5 hours. The reaction mixture was cooled to room temperature. Then, sodium carbonate (saturated solution) was added to the mixture until the pH was greater than 8. The mixture was extracted with ethyl acetate. Combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (3-5% 7N NH3 in MeOH/CH2Cl2) gave 84 mg of (4,5-Dihydro-oxazol-2-yl)-(1-phenyl-prop-2-ynyl)-amine (Formula 30) as a white solid. 1H NMR (300 MHz, CDCl3) δ 2.49 (d, J=2.0 Hz, 1H), 3.66-3.75 (m, 2H), 4.22-4.28 (m, 2H), 5.58 (d, J=2.0 Hz, 1H), 7.26-7.31 (m, 1H), 7.33-7.36 (m, 2H), 7.52-7.54 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-acc0268e23bf4eb5b74104280edccc10
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Reaction notes

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