Ethanol → N,N-dimethyl-N'-[2-(4-methylphenyl)phenyl]sulfonylmethanimidamide

HRID 1182748

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HRID 1182748 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](/[N:11]=[CH:12]/[N:13]([CH3:15])[CH3:14])(=[O:10])=[O:9].[CH3:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CCO.C1(C)C=CC=CC=1>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.CCOC(C)=O.O>[CH3:14][N:13]([CH3:15])/[CH:12]=[N:11]/[S:8]([C:3]1[C:2]([C:20]2[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=2)=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:10])=[O:9]

참가 물질

9

반응물 5

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 11779014N'-(2-bromophenyl)sulfonyl-N,N-dimethylmethanimidamide

생성물 1

HCID 9972170N,N-dimethyl-N'-[2-(4-methylphenyl)phenyl]sulfonylmethanimidamide수율 82.7%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]-benzenesulfonamide (5.4 g, 18.4 mmol), 4-methylphenylboronic acid (5.0 g, 36.8 mmol) and potassium carbonate (5.1 g, 36.8 mmol) were dissolved in water (19.7 mL, 1090 mmol), EtOH (49.2 mL, 842 mmol) and toluene (98.3 mL, 923 mmol). The resulting mixture was stirred under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was added. The mixture was heated at 60° C. for 115 minutes, at 70° C. for 30 minutes, then cooled to room temperature. Water (100 mL) and EtOAc (100 mL) were added. The mixture was washed with saturated aqueous NaCl, extracted with EtOAc, dried over MgSO4, filtered, and concentrated to yield a red solid. The product was triturated with 1:1 EtOAc:hexanes, filtered, and rinsed with hexanes to yield a reddish-brown solid. The product was triturated with EtOAc, filtered, and rinsing with EtOAc . to yield 4′-methylbiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide (4.6 g) as a light brown solid.

후처리

  1. temperaturecooled to room temperature
  2. washThe mixture was washed with saturated aqueous NaCl
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a red solid
  8. customThe product was triturated with 1:1 EtOAc
  9. filtrationhexanes, filtered
  10. washrinsed with hexanes
  11. customto yield a reddish-brown solid
  12. customThe product was triturated with EtOAc
  13. filtrationfiltered
  14. washrinsing with EtOAc

출처 및 근거

ORD 기록
ord-1fc2bc3ca0544779bb2fa9f3c103c5a4
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664227B2

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