p-Toluenesulfonic acid monohydrate → N'-(4-azido-1-phenylbutylidene)-5-chloro-2-methyl benzohydrazide

HRID 468077노트

반응식

HRID 468077 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([NH:9][NH2:10])=[O:8].[N:13]([CH2:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O)=[N+:14]=[N-:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:13]([CH2:16][CH2:17][CH2:18][C:19](=[N:10][NH:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[CH3:12])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[N+:14]=[N-:15]

참가 물질

6

반응물 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 108779184-AzidobutyrophenoneHCID 131576295-Chloro-2-methylbenzohydrazide

생성물 1

HCID 86604839N'-(4-azido-1-phenylbutylidene)-5-chloro-2-methyl benzohydrazide수율 59.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-chloro-2-methylbenzohydrazide (2.70 g, 14.62 mmol) prepared as in Example 1, Step B, in toluene (100 mL) was added 4-azido-1-phenylbutan-1-one (3.04 g, 16.1 mmol) prepared as in Example 70, Step A, followed by p-toluenesulfonic acid monohydrate (0.28 g, 1.46 mmol). The reaction was heated to reflux and stirred under a Dean-Stark trap for 16 hours. The cooled mixture was diluted with EtOAc (300 mL) and washed with NaHCO3 (100 mL). The aqueous layer was extracted with EtOAc (100 mL) and the combined organics were washed with brine (100 mL), dried over Na2SO4 and concentrated. The residue was triturated with ether and filtered to afford the product (3.09 g, 59%) as a tan solid.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. washwashed with NaHCO3 (100 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (100 mL)
  5. washthe combined organics were washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was triturated with ether
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-b9b4392e2f404ed39eeb3525b58a3d55
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623895B2

반응 노트

불러오는 중…