Hydrochloric Acid → HCID 56961402、化合物

HRID 924815ノート

反応式

HRID 924815 の反応式
[O:1]1[CH:5]=[CH:4][C:3]([C:6](=O)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:2]1.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH:21]=O)[CH3:16].[NH2:30][C:31]([NH2:33])=[O:32].Cl>CCO>[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:21]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:6]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)[NH:33][C:31](=[O:32])[NH:30]2)[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH3:16]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 13186545HCID 13186545、化合物2 回

生成物 1

HCID 56961402HCID 56961402、化合物収率 11%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
110 °C

実験手順

A mixture of 1-(furan-3-yl)-2-phenylethanone (Intermediate 22) (692 mg, 3.72 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (942 mg, 4.46 mmol), and urea (669.6 mg, 11.16 mmol) in anhydrous EtOH (5 mL) was added concentrated HCl solution (0.2 mL), and the reaction mixture was refluxed (110° C.) for thirteen hours. TLC (eluting with EtOAc) showed that the most of the starting materials were consumed. The reaction mixture was concentrated, and purified by column chromatography and preparative HPLC to afford Compound 50 as a yellow solid (173 mg, yield: 11.0%). 1H NMR (DMSO-d6 400 MHz TMS): δ10.26 (s, 1H), 8.478 (s, 1H), 6.981-7.708 (m, 10H), 5.766 (s, 1H), 5.141 (d, J=2.4 Hz, 1H), 3.918-4.061 (m, 2H), 1.304 (t, J=6.8 Hz, 3H); MS (ESI): m/z 422.1[M+1]+.

後処理

  1. washTLC (eluting with EtOAc)
  2. customwere consumed
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by column chromatography and preparative HPLC

出典と根拠

ORDレコード
ord-dbf291ca42c14ae792fe1d7757dbac8b
出典データセット
uspto-grants-2016_03
特許番号
US09283229B2

反応ノート

読み込み中…