Triethylamine → N-(5-Chloro-2-methoxyphenyl)-N'-(2-oxo-2-phenylethyl)urea

HRID 650041

반응식

HRID 650041 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([N:8]=[C:9]=[O:10])[CH:7]=1.Cl.[NH2:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([NH:8][C:9]([NH:14][CH2:15][C:16](=[O:17])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:10])[CH:7]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 1440094-Chloro-2-isocyanato-1-methoxybenzeneHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)

생성물 1

HCID 21714202N-(5-Chloro-2-methoxyphenyl)-N'-(2-oxo-2-phenylethyl)urea

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

5-Chloro-2-methoxyphenylisocyanate (5.3 g, 29 mmol) was dissolved in THF (250 ml) under N2 and heated to 60° C. To this solution was added 2-aminoacetophenone-HCl (5 g, 29 mmol) followed by triethylamine (3.8 g, 30 mmol). After being stirred 1.5 h, the reaction mixture was diluted with ethyl acetate (2 vol) and washed with 1N HCl solution, saturated NaCO3 solution, and brine before being dried, MgSO4. Concentration gave a solid which was washed with diethylether 6 g (65%). mp 171-173° C.; IR(KBr, υ=cm−1) 3336, 1706, 1644, 1600, 1560, 1482, 1262, 1220, 1182, 1126; 1H NMR (300 MHz, CDCl3) δ 3.79 (3H, s), 4.84 (2H, d, J=4.3 Hz), 5.97 (1H, br.s), 6.71 (1H, d, J=8.7 Hz), 6.88 (1H, dd, J=8.7 Hz, 2.5 Hz), 7.97-8.00 (2H, m), 8.18 (1H, d, J=2.5 Hz); MS(DCl)m/z: 319(MH+); Anal. calcd. for C16H15ClN2O3: C, 60.29; H, 4.74; N, 8.79. Found: C, 60.17; H, 4.64; N, 8.70.

후처리

  1. washwashed with 1N HCl solution, saturated NaCO3 solution, and brine
  2. custombefore being dried
  3. concentrationConcentration
  4. customgave a solid which
  5. washwas washed with diethylether 6 g (65%)

출처 및 근거

ORD 기록
ord-77c03cb0277b4a92bfb2164ced71049c
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271249B1

연결된 노트

불러오는 중…