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

HRID 1626793

반응식

HRID 1626793 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-592cbb6cc2b04eb198e76dc0694769d9
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785462B2

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