Aniline → 2-(methylthio)-N-phenylaniline

HRID 403138노트

반응식

HRID 403138 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 140448122-(methylthio)-N-phenylaniline

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

(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%)

후처리

  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

출처 및 근거

ORD 기록
ord-c95a082f2f3542ee99296d479c847c81
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748011B2

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