4-Methylmorpholine → 2-(4'-Bromobiphenyl-4-yl)-N,N-dimethylacetamide

HRID 1626793ノート

反応式

HRID 1626793 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:19][NH:20][CH3:21].[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.CN1CCOCC1>O1CCCC1.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([N:20]([CH3:21])[CH3:19])=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 10473Dimethylamine, hydrochlorideHCID 13942454'-Bromo-4-carboxymethylbiphenylHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

生成物 1

HCID 681932812-(4'-Bromobiphenyl-4-yl)-N,N-dimethylacetamide収率 76.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

(4′-Bromobiphenyl-4-yl)acetic acid (1.0 g, 3.4 mmol) was dissolved in a mixed solvent of tetrahydrofuran (20 mL) and methanol (20 mL), and dimethylamine hydrochloride (0.42 g, 5.2 mmol), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (1.3 g, 4.7 mmol) and N-methylmorpholine (0.95 mL, 8.6 mmol) were added, followed by stirring at room temperature for 18 hours. After the reaction solution was concentrated under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: dichloromethane/ethyl acetate), and a fraction corresponding to the Rf value=0.55 (dichloromethane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.82 g, 2.6 mmol) as a white solid (yield 75%).

後処理

  1. additionwere added
  2. concentrationAfter the reaction solution was concentrated under reduced pressure
  3. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: dichloromethane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.55 (dichloromethane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-592cbb6cc2b04eb198e76dc0694769d9
出典データセット
uspto-grants-2014_07
特許番号
US08785462B2

反応ノート

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