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Cesium carbonate → methyl 4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]-2-[[4-(trifluoromethoxy)benzoyl]amino]benzoate

HRID 29677
ノート
印刷プレビュー

反応式

HRID 29677 の反応式
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13]Br)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.[C:30]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:35]=[CH:34][C:33]([CH:36]=[N:37][OH:38])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:38]/[N:37]=[CH:36]/[C:33]2[CH:34]=[CH:35][C:30]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:31][CH:32]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1
参加物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 10796Cesium carbonateHCID 2615464-PhenylbenzaldoximeHCID 692101914-(3-Bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

生成物 1

HCID 87735102methyl 4-[3-[(E)-(4-phenylphenyl)methylideneamino]oxypropoxy]-2-[[4-(trifluoromethoxy)benzoyl]amino]benzoate収率 80%

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒

実験手順

This compound was produced using similar methods as those used in Step 5, example 27, starting with 4-(3-bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (0.46 g, 0.97 mmol), biphenyl-4-carbaldehyde oxime (0.20 g, 1.01 mmol) and cesium carbonate (1.26 g, 3.86 mmol) in acetone (35 mL). The crude material was purified by flash chromatography through silica gel using diethyl ether/hexanes (0/100 gradient to 12/88) to give 4-[3-({[(1E)-1,1′-biphenyl-4-ylmethylidene]amino}oxy)propoxy]-2-{[4-(trifluoromethoxy)benzoyl]amino}benzoic acid methyl ester (0.46 g, 80%) as a white solid. 1H NMR (500 MHz, DMSO-d6); δ 11.93 (s, 1H), 8.34 (d, 1H), 8.31 (s, 1H), 8.06 (d, 2H), 7.99 (d, 1H), 7.70-7.66 (m, 6H), 7.60 (d, 1H), 7.46 (t, 2H), 7.38 (t, 1H), 6.85 (dd, 1H), 4.31 (t, 2H), 4.23 (t, 2H), 3.87 (s, 3H), 2.18 (m, 2H).

後処理

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel

出典と根拠

ORDレコード
ord-7ad0965e86ef4bfb8e4dc21023266aaf
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07420083B2

反応ノート

読み込み中…

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