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

HRID 476303

反応式

HRID 476303 の反応式
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]

参加物

9

反応物 5

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

生成物 1

HCID 9972170N,N-dimethyl-N'-[2-(4-methylphenyl)phenyl]sulfonylmethanimidamide

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4b612d6875a444cf807f683c28bc8e10
出典データセット
uspto-grants-2014_01
特許番号
US08637676B2

関連ノート

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