Nitric Acid → 2-nitro-6,7-dihydrobenzo[b]thiophen-4(5H)-one

HRID 1160677노트

반응식

HRID 1160677 반응식
[CH2:1]1[CH2:10][C:8](=[O:9])[C:4]2[CH:5]=[CH:6][S:7][C:3]=2[CH2:2]1.[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[N+:11]([C:6]1[S:7][C:3]2[CH2:2][CH2:1][CH2:10][C:8](=[O:9])[C:4]=2[CH:5]=1)([O-:13])=[O:12]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 834184,5,6,7-Tetrahydro-4-oxothionaphthene

생성물 1

HCID 7628782-nitro-6,7-dihydrobenzo[b]thiophen-4(5H)-one수율 75%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매2회

반응 조건

온도
-5 °C

실험 절차

was prepared using a literature procedure (Asprou et al., J. Heterocyclic Chem., 17:87-92 (1980) (“Asprou”), which is hereby incorporated by reference). To a 50 mL round bottom flask charged with a stir bar was added 4-keto-4,5,6,7-tetrahydrothianaphthene (0.61 g, 4 mmole) and concentrated sulfuric acid (6 mL). The solution was then cooled in an ice/salt bath to −5° C. and stirred while a solution of concentrated nitric acid (0.3 mL) in concentrated sulfuric acid (3 mL) was added dropwise over 30 minutes. Solution was stirred for another 50 minutes and allowed to gradually warm to 5° C. The reaction mixture was then poured onto crushed ice and the yellow precipitate filter and washed with several portions of ice-cold water to give product as a yellow solid (0.594 g, 75% yield). Spectral data were consistent with the literature values (Asprou, which is hereby incorporated by reference).

후처리

  1. customwas prepared
  2. additionTo a 50 mL round bottom flask charged with a stir bar
  3. additionwas added dropwise over 30 minutes
  4. temperatureto gradually warm to 5° C
  5. additionThe reaction mixture was then poured
  6. customonto crushed ice
  7. filtrationthe yellow precipitate filter
  8. washwashed with several portions of ice-cold water

출처 및 근거

ORD 기록
ord-b272368ffc8a43ddbb994ff37ccc0143
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816536B2

반응 노트

불러오는 중…