Sodium Carbonate → N-(1-phenylbut-3-ynyl)-4,5-dihydrooxazol-2-amine

HRID 659134Notes

Reaction equation

HRID 659134 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][C:10]#[CH:11])=[O:6].C(=O)([O-])[O-].[Na+].[Na+]>O>[NH3:4].[C:12]1([CH:8]([NH:7][C:5]2[O:6][CH2:2][CH2:3][N:4]=2)[CH2:9][C:10]#[CH:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 574298141-(2-Chloroethyl)-3-(1-phenylbut-3-ynyl)urea2×

Product 2

HCID 222AmmoniaYield 4%HCID 44480251N-(1-phenylbut-3-ynyl)-4,5-dihydrooxazol-2-amineYield 63.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 200 mg of 1-(2-chloroethyl)-3-(1-phenylbut-3-ynyl)urea (Formula 18) in 5 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 until the pH of the solution 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 (4% 7N NH3 in CH3OH/CH2Cl2) gave 54 mg of N-(1-phenylbut-3-ynyl)-4,5-dihydrooxazol-2-amine (Formula 19) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.98-2.00 (m, 1H), 2.66-2.84 (m, 2H), 3.68-3.76 (m, 2H), 4.20-4.26 (m, 2H), 4.83-4.87 (m, 1H), 7.25-7.39 (m, 5H).

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-ae5544cfdd324a8289281b392ef15004
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Reaction notes

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