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Oxalyl chloride → 5-cyano-N-(4-trifluoromethoxy-2-chlorophenyl)-2-methoxybenzamide

HRID 558387
ノート
印刷プレビュー

反応式

HRID 558387 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:11]=1)[C:8]([OH:10])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[F:20][C:21]([F:32])([F:31])[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([Cl:30])[CH:24]=1.C(N(CC)C(C)C)(C)C>ClCCl.O1CCCC1.CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:11]=1)[C:8]([NH:27][C:26]1[CH:28]=[CH:29][C:23]([O:22][C:21]([F:20])([F:31])[F:32])=[CH:24][C:25]=1[Cl:30])=[O:10])#[N:2]
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

8

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27340842-Chloro-4-(trifluoromethoxy)anilineHCID 219425685-Cyano-2-methoxybenzoic acid

生成物 1

HCID 231415205-cyano-N-(4-trifluoromethoxy-2-chlorophenyl)-2-methoxybenzamide収率 90%

試薬・触媒・溶媒 3

HCID 6228
Dimethylformamide
溶媒
HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

5-Cyano-2-methoxybenzoic acid (0.73 g) obtained in step A, and 16 μL of N,N-dimethylformamide were dissolved in 18 mL of dichloromethane, and the solution was cooled to 0° C. To this solution, 0.54 mL of oxalyl chloride was added little by little, and the mixture was stirred for 2.7 hours at room temperature. The reaction mixture was distilled under reduced pressure, and dried to obtain a light yellow solid. This solid was added, with the use of 10 mL of tetrahydrofuran, to a solution of 0.95 g of 4-trifluoromethoxy-2-chloroaniline and 2.1 mL of N,N-diisopropylethylamine dissolved in 20 mL of tetrahydrofuran. The mixture was stirred overnight at room temperature, and then tetrahydrofuran was distilled off under reduced pressure. The resulting solid was purified by silica gel column chromatography using methylene chloride as an elution solvent, thereby obtaining 1.37 g (90%) of 5-cyano-N-(4-trifluoromethoxy-2-chlorophenyl)-2-methoxybenzamide.

後処理

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customdried
  3. customto obtain a light yellow solid
  4. stirringThe mixture was stirred overnight at room temperature
  5. distillationtetrahydrofuran was distilled off under reduced pressure
  6. customThe resulting solid was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-efb8ac4fa6d949e7a794632ee3ab3f67
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063046B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート