Nitric Acid → HCID 20096586、化合物

HRID 2221109ノート

反応式

HRID 2221109 の反応式
[CH2:1]([O:3][C:4](=[O:23])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[CH:8][CH:7]=1)[CH3:2].[N+:24]([O-])([OH:26])=[O:25]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:23])[NH:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[CH:10][C:11]=1[N+:24]([O-:26])=[O:25])[CH3:2]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 69272449HCID 69272449、化合物

生成物 1

HCID 20096586HCID 20096586、化合物収率 90%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

(4-Phtalimido-phenyl)-carbamic acid ethyl ester (99.0 g, 0.32 mol) is suspended in glacial acetic acid (1.5 L) and heated to 90° C. Fuming nitric acid (17.2 mL, 0.41 mol) is added dropwise over 30 minutes at 90-95° C. The reaction mixture is then stirred at 100° C. for 1 hour and cooled to ambient temperature. Crystallised solids are filtered off and washed with glacial acetic acid (500 mL), water (1 L) and diethylether (1 L) on the filter, then dried in vacuo to furnish 101 g (90%) of the title compound as a yellow solid. LC/MS (m/z) 355.0 (MH+); tR=3.34 min. 1H NMR (DMSO-d6): 1.25 (t, 3H); 4.16 (q, 2H); 7.81 (m, 2H); 7.93 (ddd, 2H); 7.99 (ddd, 2H); 6.15 (dd, 1H); 9.99 (s, 1H, NH).

後処理

  1. temperaturecooled to ambient temperature
  2. customCrystallised solids
  3. filtrationare filtered off
  4. washwashed with glacial acetic acid (500 mL), water (1 L) and diethylether (1 L) on the filter
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-a598cc1295104ee0a46377594a01657e
出典データセット
uspto-grants-2008_05
特許番号
US07368472B2

反応ノート

読み込み中…