Toluene → 2'-Sulfamoyl-biphenyl-4-carboxylic acid

HRID 1392787노트

반응식

HRID 1392787 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[C:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([OH:14])=[O:13].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)C>[NH2:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)(=[O:10])=[O:9]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 28012632-Bromobenzenesulfonamide

생성물 1

HCID 27605552'-Sulfamoyl-biphenyl-4-carboxylic acid수율 57.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 3283Diethyl Ether용매

실험 절차

2-Bromobenzenesulfonamide (800 mg) and 4-carboxyphenylboronic acid (563 mg) were suspended in a mixed solvent of toluene (5 ml) and water (5 ml). Tetrakis(triphenylphosphine)palladium (392 mg) and anhydrous sodium carbonate (1.08 g) were successively added to the suspension, and the mixture was heated under reflux overnight. After the reaction mixture was cooled to room temperature, diethyl ether and water were added to conduct liquid separation. The resultant organic layer was extracted twice with water. The resultant water layers were all combined, and 12N hydrochloric acid was added to this solution to acidify it. The solution was concentrated to about 20 ml under reduced pressure. Colorless powder deposited was collected by filtration and dried under reduced pressure to obtain the title compound (539 mg).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customliquid separation
  4. extractionThe resultant organic layer was extracted twice with water
  5. addition12N hydrochloric acid was added to this solution
  6. concentrationThe solution was concentrated to about 20 ml under reduced pressure
  7. filtrationColorless powder deposited was collected by filtration
  8. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-bc99965c81c849a19ec6aa2d5ce765e5
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342014B2

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