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Potassium Carbonate → ethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]-5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate

HRID 623700
ノート
印刷プレビュー

反応式

HRID 623700 の反応式
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][C:8]1[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:10][NH:11][N:12]=1.C(=O)([O-])[O-].[K+].[K+].F[C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:31]=1[N+:40]([O-:42])=[O:41]>CN(C)C=O>[N+:40]([C:31]1[CH:32]=[C:33]([C:36]([F:37])([F:38])[F:39])[CH:34]=[CH:35][C:30]=1[N:11]1[N:10]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:7][C:6]2[CH:18]=[CH:19][CH:20]=[C:4]([O:3][C:2]([F:1])([F:21])[F:22])[CH:5]=2)=[N:12]1)([O-:42])=[O:41]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 178470504HCID 178470504、化合物2 回

生成物 1

HCID 90109335ethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]-5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of ethyl 5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step E, 0.55 g, 1.7 mmol) in N,N-dimethylformamide (5 mL) was added anhydrous potassium carbonate (0.48 g, 3.5 mmol) and 4-fluoro-3-nitrobenzotrifluoride (0.29 mL, 2.1 mmol). The mixture was heated to 80° C. with stirring for 90 min. The reaction mixture was concentrated to dryness under reduced pressure. The resulting residue was diluted with water (10 mL) and extracted with ethyl acetate (30 mL, 15 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to obtain the title compound (0.76 g) as a pale yellow oil.

後処理

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. additionThe resulting residue was diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (30 mL, 15 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customThe crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-ae90cb27957c40c3aec800f64334b190
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09302999B2

反応ノート

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