Sodium Azide → 3-Chloro-N-isopropyl-5-methoxy-N-[2-(1-methyl-1H-tetrazol-5-yl)ethyl]-benzamide

HRID 2268600노트

반응식

HRID 2268600 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1)[C:5]([N:7]([CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:9][C:10](=O)[NH:11][CH3:12])=[O:6].[N-:22]=[N+:23]=[N-:24].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1)[C:5]([N:7]([CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:9][C:10]1[N:11]([CH3:12])[N:24]=[N:23][N:22]=1)=[O:6]

참가 물질

5

반응물 3

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 183491573-Chloro-N-isopropyl-5-methoxy-N-(2-methylcarbamoyl-ethyl)-benzamide

생성물 1

HCID 183489363-Chloro-N-isopropyl-5-methoxy-N-[2-(1-methyl-1H-tetrazol-5-yl)ethyl]-benzamide수율 35.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 3-chloro-N-isopropyl-5-methoxy-N-(2-methylcarbamoyl-ethyl)-benzamide (0.312 g) in anhydrous dichloromethane (5.0 ml) was added sodium azide (0.065 g) and the mixture cooled to 0° C. Trifluoromethanesulphonic anhydride (0.200 ml) was added and the reaction stirred at room temperature for 18 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was removed and the organic layer dried with brine and over sodium sulphate and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with ethyl acetate:petroleum ether (4:1 v/v); to give the title compound as a white solid (0.121 g).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe aqueous layer was removed
  3. dry with materialthe organic layer dried with brine and over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography
  6. washeluting with ethyl acetate:petroleum ether (4:1 v/v)

출처 및 근거

ORD 기록
ord-cd1a111fc0484ae7969a99fa6268286e
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326386B1

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