Potassium Carbonate → HCID 9956212, 화합물

HRID 1493499노트

반응식

HRID 1493499 반응식
[C:1]([OH:4])(=[O:3])[CH3:2].C[C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21].[C:22](=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[CH3:22][O:3][C:1](=[O:4])[CH2:2][C:8]1[CH:9]=[C:10]([O:12][CH2:29][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=2)[CH:11]=[CH:6][C:7]=1[NH:13][C:14]1[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=1[Cl:20]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 67868427HCID 67868427, 화합물

생성물 1

HCID 9956212HCID 9956212, 화합물

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 6342Acetonitrile용매

실험 절차

Under an atmosphere of nitrogen, a mixture of the crude phenol of Step F, above (5.0 g, 15.4 mmol), potassium carbonate (1.3 g, 9.8 mmol), 18-crown-6 (130 mg), and 2-chloromethyl quinoline (4.1 g, 23 mmol) in 50 mL of acetonitrile is stirred at 60° C. for 24 hours (TLC, silica, dichloromethaneMeOH 19:1). The solvent is evaporated and the residue partitioned between ethyl acetate and water (75 mL each). The insolubles are filtered, the layers separated and the organic phase washed with 1N NaOH and brine. After drying (MgSO4) the solvent is removed in vacuo to give 7.0 g of a thick brown oil. The crude product is purified by flash chromatography (silica Merck 60, dichloromethane and dichloromethane-ethyl acetate 19:1) to give the product (4.2 g, clear oil). The oil is triturated with ethanol to give crystalline product (3.98 g, 55.5%, m.p. 90°-91° C., white solid).

후처리

  1. customThe solvent is evaporated
  2. customthe residue partitioned between ethyl acetate and water (75 mL each)
  3. filtrationThe insolubles are filtered
  4. customthe layers separated
  5. washthe organic phase washed with 1N NaOH and brine
  6. dry with materialAfter drying (MgSO4) the solvent
  7. customis removed in vacuo

출처 및 근거

ORD 기록
ord-1deed4e3ab034980b46a319222285040
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05021576

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