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

HRID 659134노트

반응식

HRID 659134 반응식
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

참가 물질

5

반응물 2

HCID 10340Sodium CarbonateHCID 574298141-(2-Chloroethyl)-3-(1-phenylbut-3-ynyl)urea2회

생성물 2

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ae5544cfdd324a8289281b392ef15004
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080570B2

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