Sodium Hydroxide → 2-Ethyl-benzofuran-3-carboxylic acid [5-bromo-6-(1H-tetrazol-5-ylmethoxy)-naphthalen-2-ylmethyl]-methyl-amide

HRID 1357257노트

반응식

HRID 1357257 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]([CH3:31])[C:18]([C:20]1[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:21]=1[CH2:29][CH3:30])=[O:19])=[CH:7]2.[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[NH:34][N:33]=[N:32][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:31])[C:18]([C:20]1[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:21]=1[CH2:29][CH3:30])=[O:19])=[CH:7]2

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 120835692-Ethyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide

생성물 1

HCID 1784380942-Ethyl-benzofuran-3-carboxylic acid [5-bromo-6-(1H-tetrazol-5-ylmethoxy)-naphthalen-2-ylmethyl]-methyl-amide수율 56%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-ethyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (0.25 g, 0.5237 mmol), prepared in the previous step, sodium azide (0.10 g, 1.57 mmol) and ammonium chloride (0.084 g, 1.57 mmol) in 12 mL DMF was stirred under nitrogen at 100° C. for 5 h. The reaction was diluted with water, made basic with 1N NaOH and extracted four times with ethyl acetate. The combined organic extracts were acidified with 1N HCl, the solvent removed under reduced pressure and the resulting residue diluted with water. The solid foam that formed was collected by filtration and dried under reduced pressure to give the title compound (0.15 g, 56%) as a tan foam, MS m/z: 520 [M+H]+.

후처리

  1. extractionextracted four times with ethyl acetate
  2. customthe solvent removed under reduced pressure
  3. additionthe resulting residue diluted with water
  4. customThe solid foam that formed
  5. filtrationwas collected by filtration
  6. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-612cb19ac455486a94daeacf2a47f4e8
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06589970B2

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