Nitric Acid → Methyl 2-[(6-chloro-5-nitro-1,2-benzisoxazol-3-yl)oxy]propionate

HRID 375066ノート

反応式

HRID 375066 の反応式
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:21]=[CH:20][C:9]2[C:10]([O:13][CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[N:11][O:12][C:8]=2[CH:7]=1>S(=O)(=O)(O)O.CCOCC.C(Cl)Cl>[Cl:5][C:6]1[C:21]([N+:1]([O-:4])=[O:2])=[CH:20][C:9]2[C:10]([O:13][CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[N:11][O:12][C:8]=2[CH:7]=1

参加物

6

反応物 2

HCID 944Nitric AcidHCID 22402920Methyl 2-[(6-chloro-1,2-benzisoxazol-3-yl)oxy]propionate

生成物 1

HCID 22402917Methyl 2-[(6-chloro-5-nitro-1,2-benzisoxazol-3-yl)oxy]propionate

試薬・触媒・溶媒 3

HCID 1118Sulfuric Acid溶媒HCID 3283Diethyl Ether溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

Nitric acid (70%, 3.0 mL, 47 mmol) is slowly added to a mixture of methyl 2-[(6-chloro-1,2-benzisoxazol-3-yl)oxy]propionate (6.0 g, 23.5 mmol) in concentrated sulfuric acid (50 mL) while maintaining the temperature below 10° C. The reaction mixture is stirred for 1 hour on an ice/water bath and poured onto ice. The resultant aqueous mixture is diluted with ether, stirred for several minutes and the ether is allowed to evaporate overnight. The resultant mixture is filtered to obtain a solid which is dissolved in methylene chloride. The methylene chloride solution is dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a solid which is recrystallized from an ether/hexanes solution to give the title product as a solid, mp 98°-101° C.

後処理

  1. temperaturewhile maintaining the temperature below 10° C
  2. additionpoured onto ice
  3. stirringstirred for several minutes
  4. customto evaporate overnight
  5. filtrationThe resultant mixture is filtered
  6. customto obtain a solid which
  7. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto obtain a solid which
  10. customis recrystallized from an ether/hexanes solution

出典と根拠

ORDレコード
ord-d911a736d8874a48a16cb9fb525b945a
出典データセット
uspto-grants-1996_01
特許番号
US05484763

反応ノート

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