2-Bromo-naphtho[2,3-b]furan-4,9-dione → 2-Methylthio-naphtho[2,3-b]furan-4,9-dione

HRID 540652노트

반응식

HRID 540652 반응식
Br[C:2]1[O:6][C:5]2[C:7](=[O:16])[C:8]3[C:13]([C:14](=[O:15])[C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C(S)[CH2:18][S:19]([O-])(=O)=O.[Na+]>O1CCCC1.O>[CH3:18][S:19][C:2]1[O:6][C:5]2[C:7](=[O:16])[C:8]3[C:13]([C:14](=[O:15])[C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

참가 물질

5

반응물 2

HCID 3962872-Bromo-naphtho[2,3-b]furan-4,9-dioneHCID 23662354Mesna

생성물 1

HCID 107766732-Methylthio-naphtho[2,3-b]furan-4,9-dione수율 90.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To the solution of 0.7 gram (2.5 mmoles) of 2-bromo-naphtho[2,3-b]furan-4,9-dione in 20 mL of tetrahydrofuran at room temperature, 0.4 grams (5.0 mmoles) of MeSNa in 5 mL of water was added dropwise over 1 minute. The mixture was further stirred for 2 hours at room temperature, and then evaporated to remove tetrahydrofuran. To the residue, 20 mL of 1N hydrochloric acid was added, and the resulting mixture was filtered. The solid was washed with water, and then crystallized in ethanol/water. Pure crystal product was filtered and dried under vacuum. 0.55 grams of product (yield 90%) was obtained and characterized by 1H NMR and mass spectrum. 1H NMR (in CDCl3) δ 2.66 (s, 3H), 6.79 (s, 1H), 7.75-7.79 (m, 2H), 8.18-8.25 (m, 2H). Mass (M+H) is 245.

후처리

  1. customevaporated
  2. customto remove tetrahydrofuran
  3. additionTo the residue, 20 mL of 1N hydrochloric acid was added
  4. filtrationthe resulting mixture was filtered
  5. washThe solid was washed with water
  6. customcrystallized in ethanol/water
  7. filtrationPure crystal product was filtered
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-ced5cc5c55bd4c3b8a67026cd95b98e1
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871802B2

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