Water → 3-[(Carboxyphenyl)sulfanyl]benzenecarboxylic acid

HRID 2055917노트

반응식

HRID 2055917 반응식
I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11](=[O:14])([O-])[O-:12].[K+].[K+].[S-2:17].[Na+].[Na+].O>CN(C=O)C.[Cu](I)I>[C:5]([C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][C:3]=1[S:17][C:2]1[CH:10]=[C:9]([C:11]([OH:12])=[O:14])[CH:8]=[CH:4][CH:3]=1)([OH:7])=[O:6]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 120603-Iodobenzoic acidHCID 14804Sodium Sulfide

생성물 1

HCID 166410023-[(Carboxyphenyl)sulfanyl]benzenecarboxylic acid수율 39.1%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 3-iodobenzoic acid (24.8 g, 100.0 mmol) was dissolved in anhydrous DMF (100.0 mL) was added potassium carbonate (6.9 g, 50.0 mmol). The reaction mixture was heated to 100° C. for 5 minutes and sodium sulphide (4.3 g, 55.0 mmol) and copper iodide (1.9 g, 10.0 mmol) was added and the reaction mixture was heated to reflux under an atmosphere of nitrogen for 12 hours. Water (500.0 mL) was then added and the reaction mixture was heated to boiling with activated carbon. The carbon was filtered off while hot into an excess of 6N HCl (50.0 mL). A precipitate formed on cooling to room temperature and was collected by filtration and washed with water to afford (5.36 g, 19.5%) of the desired 3-[(carboxyphenyl)sulfanyl]benzenecarboxylic acid (GM71/7) as an off-white powder. M.S. m/z 272.73 (M−1)+. 1H NMR (300.13, d6-DMSO) 7.32-7.63 (4H, m, 4×ArH), 7.84-7.99 (4H, m, 4×ArH).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux under an atmosphere of nitrogen for 12 hours
  3. temperaturethe reaction mixture was heated
  4. filtrationThe carbon was filtered off while hot into an excess of 6N HCl (50.0 mL)
  5. customA precipitate formed
  6. temperatureon cooling to room temperature
  7. filtrationwas collected by filtration
  8. washwashed with water

출처 및 근거

ORD 기록
ord-f82f69463a074b0c86001a3d3f4995f1
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07332631B2

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