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Phosphorus oxychloride → 4-(2,4-dichlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)-2-morpholin-4-ylthiophene-3-carbonitrile

HRID 2091687
ノート
印刷プレビュー

反応式

HRID 2091687 の反応式
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[C:10]([C:20]#[N:21])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])=O.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[C:11]1[C:10]([C:20]#[N:21])=[C:9]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[S:8][C:7]=1[C:5]1[NH:4][CH2:3][CH2:2][N:1]=1
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

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 67073109N-(2-aminoethyl)-4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxamide

生成物 1

HCID 685293044-(2,4-dichlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)-2-morpholin-4-ylthiophene-3-carbonitrile収率 95.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

To a suspension of N-(2-aminoethyl)-4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxamide (2.50 g, 5.90 mmol) in toluene (20 mL) was added phosphoryl chloride (4.70 mL, 50.0 mmol) and the mixture was stirred under microwave irradiation at 120° C. for 25 minutes. The reaction mixture was evaporated and the residue was suspended in methylene chloride and then quenched with ice water. The aqueous layer was basified by addition of KOH, the layers were separated and the aqueous layer was extracted again with methylene chloride. The organic layers were combined and washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the crude product (2.3 gr, 77%). LCMS: (FA) ES+ 408. 1H NMR (400 MHz, d6-DMSO) δ: 7.78-7.75 (m, 1H), 7.52-7.49 (m, 2H), 3.79-3.73 (m, 4H), 3.63-3.55 (m, 2H), 3.54-3.48 (m, 4H), 3.20-3.11 (m, 2H).

後処理

  1. customThe reaction mixture was evaporated
  2. customquenched with ice water
  3. additionThe aqueous layer was basified by addition of KOH
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted again with methylene chloride
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a65bfd1fdc4d4d1193a588c257941aeb
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08440664B2

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