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

HRID 2113746노트

반응식

HRID 2113746 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2babcd1b89fb4a15bf99ed12987f76c0
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432288B2

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