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Ammonium Chloride → HCID 178482586, 화합물

HRID 1357278
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HRID 1357278 반응식
[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]#[N:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:30])[C:18]([C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH3:29])[CH:21]=1)=[O:19])=[CH:7]2.[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[NH:33][N:32]=[N:31][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:30])[C:18]([C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH3:29])[CH:21]=1)=[O:19])=[CH:7]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 120835741-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide

생성물 1

HCID 178482586HCID 178482586, 화합물수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (1.0 g, 2.0 mmol), prepared in the previous step, sodium azide (0.32 g, 6.0 mmol) and ammonium chloride (0.39 g, 6.0 mmol) in 15 mL of DMF was stirred under nitrogen at 100° C. for 6 h. The reaction was partitioned between ethyl acetate and water. The aqueous layer was made basic by the addition of 1 N NaOH. The organic layer was separated and the aqueous layer extracted five times with ethyl acetate. The aqueous layer was then acidified with 1N HCl. After 2 h a white solid had precipitated from solution. The solid was collected by filtration and dried under reduced pressure to give the title compound (0.8460 g, 84%) as an off-white solid, mp 227-228° C.

후처리

  1. customThe reaction was partitioned between ethyl acetate and water
  2. additionThe aqueous layer was made basic by the addition of 1 N NaOH
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted five times with ethyl acetate
  5. customAfter 2 h a white solid had precipitated from solution
  6. filtrationThe solid was collected by filtration
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-f258b715facd431d81a5f5e4808e22e5
출처 데이터셋
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06589970B2

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