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Toluene → Mandipropamid

HRID 2112301
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HRID 2112301 반응식
[CH2:1](Br)[C:2]#[CH:3].[C:5]1(C)[CH:10]=CC=C[CH:6]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:34])[C:20]([NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([O:32][CH3:33])[CH:26]=2)=[O:21])=[CH:15][CH:14]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC(Cl)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([O:34][CH2:10][C:5]#[CH:6])[C:20]([NH:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:1][C:2]#[CH:3])=[C:27]([O:32][CH3:33])[CH:26]=2)=[O:21])=[CH:17][CH:18]=1
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참가 물질

7

반응물 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 179554462-(4-Chlorophenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

생성물 1

HCID 11292824Mandipropamid

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide
촉매
HCID 63651,1-Dichloroethane용매

실험 절차

A 80% solution of propargyl bromide in toluene (39,1 g, 0,263 mol) is added slowly at room temperature to a mixture of 2-(4-chloro-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide (35.25 g, 0,105 mol), 30% sodium hydroxide solution (52,4 ml, 0,524 mmol) and tetrabutylammonium bromide (1,8 g) in 180 ml of dichloroethane. The reaction mixture is stirred for 16 hours at +40° C. Subsequently the mixture is evaporated and the residue is diluted with water (100 ml) and dichloroethane (100 ml). The organic phase is separated and the aqueous layer is extracted with dichloroethane. The combined organic phases are washed with brine (150 ml), dried over sodium sulfate and evaporated. The remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 1:1) to yield 2-(4-chloro-phenyl)-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide, m.p. 90-92° C.

후처리

  1. customSubsequently the mixture is evaporated
  2. additionthe residue is diluted with water (100 ml) and dichloroethane (100 ml)
  3. customThe organic phase is separated
  4. extractionthe aqueous layer is extracted with dichloroethane
  5. washThe combined organic phases are washed with brine (150 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe remaining oil is purified by chromatography on silica gel (ethyl acetate/hexane 1:1)

출처 및 근거

ORD 기록
ord-4eed6f6ef4484de0a2bb28667add143f
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07521579B2

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