Pivalaldehyde → N-(1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethylpropyl)-4-methylbenzamide

HRID 479502

반응식

HRID 479502 반응식
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7]([NH2:9])=[O:8])=[CH:3][CH:2]=1.[CH3:11][C:12]([CH:15]=O)([CH3:14])[CH3:13].[NH:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:17]1([CH:15]([NH:9][C:7](=[O:8])[C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)[C:12]([CH3:13])([CH3:14])[CH3:11])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1

참가 물질

6

반응물 3

HCID 12417PivalaldehydeHCID 692744-MethylbenzamideHCID 178418385HCID 178418385, 화합물

생성물 1

HCID 11450124N-(1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethylpropyl)-4-methylbenzamide수율 68.1%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

A suspension of p-toluamide (4.11 g, 30.4 mmol), pivaldehyde (2.62 g, 30.4 mmol), and benzotriazole (3.62 g, 30.4 mmol) in toluene (200 mL) were treated with p-toluenesulfonic acid (286 mg, 1.52 mmol). The solution was heated at reflux under Dean-Stark conditions for 10 hours, cooled gradually to ambient temperature, and further cooled at 5° C. The white precipitate which formed was collected by filtration and was washed with 50% ether/hexanes (100 mL) to provide 6.67 g of the desired product as a white solid.

후처리

  1. temperatureThe solution was heated
  2. temperatureat reflux under Dean-Stark conditions for 10 hours
  3. temperaturefurther cooled at 5° C
  4. customThe white precipitate which formed
  5. filtrationwas collected by filtration
  6. washwas washed with 50% ether/hexanes (100 mL)

출처 및 근거

ORD 기록
ord-244ce3fff0da49f88668755d477f9b8e
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645968B2

연결된 노트

불러오는 중…