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

HRID 650041ノート

反応式

HRID 650041 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-77c03cb0277b4a92bfb2164ced71049c
出典データセット
uspto-grants-2001_08
特許番号
US06271249B1

反応ノート

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