4-Methylmorpholine → (4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone

HRID 2053752노트

반응식

HRID 2053752 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=N1.CN1CCOCC1.N1CC=CC1>CN(C)C=O>[N:19]1([C:6]([C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=2[CH3:11])=[O:8])[CH2:20][CH:25]=[CH:24][CH2:23]1

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 660593-PyrrolineHCID 995704-Bromo-2-methylbenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

생성물 1

HCID 22600480(4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

25.0 g (0.12 mol) of 4-bromo-2-methylbenzoic acid is dissolved in 250 mL of dimethylformamide and after the addition of 41.7 g (0.13 mol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), 14.3 mL (0.13 mol) of N-methylmorpholine and 9.6 mL (0.12 mol) of 2,5-dihydropyrrole, the mixture is stirred for 16 hours at ambient temperature. Then it is poured onto ice water and extracted with ethyl acetate. The combined organic extracts are washed with sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated by evaporation. Yield: 31.6 g (97% of theory); Rf value: 0.45 (silica gel; dichloromethane/ethanol=19:1).

후처리

  1. additionThen it is poured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed with sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-13068a93f2ec4ec2ac10d0c3f94f8be7
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326791B2

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