Aniline → 2-(methylthio)-N-phenylaniline

HRID 403138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403138
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC(C)([O-])C.[Na+].[NH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:9][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Komponenten

7

Edukt 4

HCID 6115AnilineHCID 881662-BromothioanisoleHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxide

Produkt 1

HCID 140448122-(methylthio)-N-phenylaniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

(2-bromophenyl)(methyl)sulfane (25 g, 123 mmol), Pd2dba3 (6.75 g, 7.38 mmol), S-Phos (6.06 g,14.77 mmol) and sodium tert-butoxide (17.74 g, 185 mmol) were placed in a dry 3 neck flask under N2. The reaction mixture was vacuum evacuated and back filled with N2 three times. Aniline (22.93 g, 246 mmol) and 500 mL toluene were added to the reaction mixture. The reaction mixture was refluxed for 18 hours. The crude reaction mixture was run through a silica gel plug and eluted with toluene. The toluene portion was concentrated down and subjected to a silica gel column by using 3-5% DCM in hexanes to yield desired product. (24 g, 111 mmol, 91%)

Aufarbeitung

  1. customa dry 3 neck flask under N2
  2. customevacuated
  3. additionback filled with N2 three times
  4. temperatureThe reaction mixture was refluxed for 18 hours
  5. customThe crude reaction mixture
  6. washeluted with toluene
  7. concentrationThe toluene portion was concentrated down

Quellen und Nachweise

ORD-Eintrag
ord-c95a082f2f3542ee99296d479c847c81
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748011B2

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