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

HRID 2268600ノート

反応式

HRID 2268600 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cd1a111fc0484ae7969a99fa6268286e
出典データセット
uspto-grants-2001_12
特許番号
US06326386B1

反応ノート

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