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Triethylamine → Ibrolipim

HRID 1090067
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HRID 1090067 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.C(N(CC)C1C=CN=CC=1)C.[CH2:29]([O:31][P:32]([CH2:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)([O:34][CH2:35][CH3:36])=[O:33])[CH3:30]>ClCCl.O>[CH2:35]([O:34][P:32]([CH2:37][C:38]1[CH:39]=[CH:40][C:41]([C:42]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=2[C:4]#[N:5])=[O:43])=[CH:45][CH:46]=1)([O:31][CH2:29][CH3:30])=[O:33])[CH3:36]
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 4297402-Amino-5-bromobenzonitrileHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chlorideHCID 117687514-Diethylaminopyridine

생성물 1

HCID 131601Ibrolipim

시약·촉매·용매 2

HCID 962Water용매
HCID 6344
Dichloromethane
용매
2회

실험 절차

3.94 Grams (20 mM) of 2-amino-5-bromobenzonitrile, 2.22 g (22 mM) of triethylamine and 0.49 g (4 mM) of 4-diethylaminopyridine were dissolved in 40 ml of anhydrous dichloromethane. To this solution was added dropwise 40 ml of anhydrous dichloromethane solution with 5.81 g (20 mM) of 4-diethoxyphosphinoylmethylbenzoyl chloride at 0° C. with stirring. After the stirring was continued for 10 hours at room temperature, 50 ml of water was added to the reaction mixture, and the whole mixture was extracted with chloroform. The chloroform extracts were dried over anhydrous sodium sulfate and concentrated. Thus obtained residue was purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:2). The crude crystals were recrystallized from benzene-n-hexane to yield 2.94 g of 4-diethoxyphosphinoylmethyl-N-(4-bromo-2-cyanophenyl)benzamide as colorless crystals.

후처리

  1. extractionthe whole mixture was extracted with chloroform
  2. dry with materialThe chloroform extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThus obtained residue was purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:2)
  5. customThe crude crystals were recrystallized from benzene-n-hexane

출처 및 근거

ORD 기록
ord-43060edbba47469c855c06a69af44138
출처 데이터셋
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05081112

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