홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Dimethyl Sulfoxide → 2-Benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehyde

HRID 750263
노트
인쇄 미리보기

반응식

HRID 750263 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[C:27]([CH2:28][OH:29])=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Br:36])[CH:24]=2)[C:19]1=[O:37])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C1COCC1.O>[CH2:11]([N:18]1[C:27]([CH:28]=[O:29])=[C:26]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Br:36])[CH:24]=2)[C:19]1=[O:37])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 230609532-benzyl-6-bromo-3-hydroxymethyl-4-phenyl-2H-isoquinolin-1-one

생성물 1

HCID 230605422-Benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehyde수율 62.6%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매3회

실험 절차

Under a nitrogen stream, to a solution of oxalyl chloride (0.54 ml) in THF (28 ml) was added dropwise a solution of DMSO (0.58 ml) in THF (5 ml) at −70° C. or below and the mixture was stirred for 10 min. A solution of 2-benzyl-6-bromo-3-hydroxymethyl-4-phenyl-2H-isoquinolin-1-one (1.30 g) in THF (7 ml) was added dropwise at −70° C. or below and the mixture was stirred at −60° C. to −50° C. for 1 hr. To the reaction mixture was added dropwise triethylamine (3.1 ml) at 50° C. or below and the mixture was allowed to warm to room temperature and stirred for 30 min. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from ethyl acetate-hexane to give the title compound (810 mg).

후처리

  1. stirringthe mixture was stirred at −60° C. to −50° C. for 1 hr
  2. stirringstirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was crystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-db44c299562f4bea80090e95d41dd899
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07402595B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트