N-Methylethylenediamine → (1-Methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester

HRID 48321

반응식

HRID 48321 반응식
[CH2:1]([O:3][P:4]([CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1F)=O)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[CH3:19][NH:20][CH2:21][CH2:22][NH2:23]>N1C=CC=CC=1>[CH2:1]([O:3][P:4]([CH:9]=[C:10]1[NH:23][CH2:22][CH2:21][N:20]([CH3:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]1=2)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

참가 물질

4

반응물 2

HCID 8014N-MethylethylenediamineHCID 86585808Diethyl [2-(2-Fluorophenyl)-2-oxoethyl]phosphonate

생성물 1

HCID 72957243(1-Methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester수율 26.6%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
95 °C

실험 절차

A mixture of 10.45 g (38.1 mmol) of [2-(2-fluorophenyl)-2-oxoethyl]phosphonic acid diethyl ester and 14.1 g (190 mmol) N-methylethylenediamine in 100 ml of pyridine was heated at 95° C. for 18 hours. The solvent was evaporated and the residue was partitioned between 200 ml of water and 2×100 ml of dichloromethane. The combined organic portions were dried (magnesium sulphate), filtered and evaporated. The residue was purified by column chromatography eluting with 5% methanol/dichloromethane to give 3.14 g (26%) of (1-methyl-1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-ylidenemethyl)phosphonic acid diethyl ester as a light brown oil; MS: m/e 311.0 [M+H]+.

후처리

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between 200 ml of water and 2×100 ml of dichloromethane
  3. dry with materialThe combined organic portions were dried (magnesium sulphate)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with 5% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-deca01e94d734623854fc9a21f58b731
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703387B2

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