(2-(Methylthio)ethyl)amine → 3-Chloro-1-[2-(methylsulfanyl)ethyl]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113746ノート

反応式

HRID 2113746 の反応式
[Cl:1][C:2]1[C:3](=[O:14])O[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:15][S:16][CH2:17][CH2:18][NH2:19]>C(O)(=O)C>[Cl:1][C:2]1[C:3](=[O:14])[N:19]([CH2:18][CH2:17][S:16][CH3:15])[C:5](=[O:13])[C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 87697(2-(Methylthio)ethyl)amineHCID 234471953-Chloro-4-phenylfuran-2,5-dione

生成物 1

HCID 691478763-Chloro-1-[2-(methylsulfanyl)ethyl]-4-phenyl-1H-pyrrole-2,5-dione収率 54%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 3-chloro-4-phenylfuran-2,5-dione (1.00 mmol, 209 mg) and 2-aminoethyl methyl sulphide (1.00 mmol, 91 mg) in glacial acetic acid (2 mL) was heated in a microwave reactor at 120° C. for two min. After cooling, the solvent was evaporated at reduced pressure. The residue was partitioned between water and CH2Cl2. The organic phase was evaporated and the crude product was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN) to give 152 mg (54%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 7.97-7.90 (m, 2H), 7.53-7.47 (m, 3H), 3.86 (t, J=6.8 Hz, 2H), 2.78 (t, J=6.8 Hz, 2H), 2.16 (s, 3H).

後処理

  1. temperatureAfter cooling
  2. customthe solvent was evaporated at reduced pressure
  3. customThe residue was partitioned between water and CH2Cl2
  4. customThe organic phase was evaporated
  5. customthe crude product was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

出典と根拠

ORDレコード
ord-2babcd1b89fb4a15bf99ed12987f76c0
出典データセット
uspto-grants-2008_10
特許番号
US07432288B2

反応ノート

読み込み中…