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

HRID 1496717

반응식

HRID 1496717 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]sulfonylmethanimidamide

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

2-Bromo-N-[1-dimethylaminometh-(E)-ylidene]benzenesulfonamide (5.36 g, 18.4 mmol), 4-methylphenylboronic acid (5.0 g, 36.8 mmol), potassium carbonate (5.1 g, 36.8 mmol), water (19.7 mL, 1090 mmol), EtOH (49.2 mL, 842 mmol) and toluene (98.3 mL, 923 mmol) were combined and the mixture was stirred under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was then added. The mixture was heated at 60° C. for about 2 hours, then heated at 70° C. for 30 minutes. The mixture was then cooled to room temperature and water (100 mL) and EtOAc (100 mL) were added. The mixture was washed with saturated aqueous NaCl, extracted with EtOAc, dried over MgSO4, filtered through Celite® and concentrated to yield the crude product as a red solid (8.6 g). The solid material was triturated with 1:1 EtOAc:hexanes, filtered, and rinsed with hexanes to yield the crude product as a reddish-brown solid (6.2 g). The solid material was again triturated with EtOAc, filtered, and rinsed with EtOAc to yield 4′-methybiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide as a light brown solid (4.6 g; 96.2% purity).

후처리

  1. temperatureheated at 70° C. for 30 minutes
  2. temperatureThe mixture was then cooled to room temperature
  3. washThe mixture was washed with saturated aqueous NaCl
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through Celite®
  7. concentrationconcentrated
  8. customto yield the crude product as a red solid (8.6 g)
  9. customThe solid material was triturated with 1:1 EtOAc
  10. filtrationhexanes, filtered
  11. washrinsed with hexanes
  12. customto yield the crude product as a reddish-brown solid (6.2 g)
  13. customThe solid material was again triturated with EtOAc
  14. filtrationfiltered
  15. washrinsed with EtOAc

출처 및 근거

ORD 기록
ord-bb77b27a53b44542b21fb2ac560dc743
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198899B2

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