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Potassium Carbonate → 1-[2-(2,6-Dichlorophenylamino)phenyl]-N-[2-(2-hydroxyethoxy)-ethyl]methanesulfonamide

HRID 1259039
ノート
印刷プレビュー

反応式

HRID 1259039 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9]([NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])(=[O:11])=[O:10].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1Br.C([O-])([O-])=O.[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.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]>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9]([NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])(=[O:11])=[O:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 295681-Bromo-2,6-dichlorobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 625000681-(2-aminophenyl)-N-[2-(2-hydroxyethoxy)ethyl]methanesulfonamide

生成物 1

HCID 426408781-[2-(2,6-Dichlorophenylamino)phenyl]-N-[2-(2-hydroxyethoxy)-ethyl]methanesulfonamide

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
160 °C

実験手順

To a stirred solution of 1-(2-aminophenyl)-N-[2-(2-hydroxyethoxy)ethyl]-methanesulfonamide (100 mg, 0.37 mmol), 1,3-dichloro-2-bromobenzene (103 mg, 0.46 mmol), K2CO3 (126 mg, 0.99 mmol) and XantPhos (21 mg, 0.04 mmol) in 1,4-dioxane (2 ml) under nitrogen in a microwave tube was added Pd2dba3 (17 mg, 0.019 mmol) in one portion and the tube sealed. The reaction was heated with stirring in a microwave at 160° C. for 30 minutes. The reaction was cooled before filtering through celite. The crude reaction mixture was purified by column chromatography eluting with ethyl acetate:hexane to afford 1-[2-(2,6-Dichlorophenylamino)phenyl]-N-[2-(2-hydroxyethoxy)-ethyl]methanesulfonamide as product (50.5 mg, 33%); Rf (ethyl acetate:hexane 1:1) 0.11; δH (400 MHz, CDCl3) 7.34 (3H, m), 7.23 (1H, t), 7.19 (1H, s), 7.02 (2H, m), 6.60 (1H, d), 5.70 (1H, s), 4.56 (2H, s), 3.70 (2H, s), 3.56 (4H, m), 3.29 (2H, dt) and 2.83 (1H, s); LCMS Rt=3.97 min, m/z (ES+) 441 (M+Na).

後処理

  1. customthe tube sealed
  2. temperatureThe reaction was heated
  3. temperatureThe reaction was cooled
  4. filtrationbefore filtering through celite
  5. customThe crude reaction mixture
  6. customwas purified by column chromatography
  7. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-5ff088555c104da2a6f1f498eadb9465
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08466201B2

反応ノート

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