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Phosphorus pentachloride → phenyl 2-methyl-N-phenyl-3-(phenylthio)thioacrylimidate

HRID 2061009
ノート
印刷プレビュー

反応式

HRID 2061009 の反応式
[CH3:1]/[C:2](=[CH:12]\[S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)/[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[Na].[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:1][C:2](=[CH:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([S:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 24819Phosphorus pentachlorideHCID 59498330(E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamideHCID 66586497Sodium benzenethiol

生成物 1

HCID 67543149phenyl 2-methyl-N-phenyl-3-(phenylthio)thioacrylimidate収率 36.9%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒
HCID 6228
Dimethylformamide
溶媒

実験手順

To a suspension of 0.8 g (3 mmol) of (E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamide in toluene (4 ml) was added 0.62 g (3 mmol) of phosphorus pentachloride and the mixture was stirred at room temperature for 4 hours. After concentration of the mixture under vacuum, the residue was dissolved in 35 ml of N,N-dimethylformamide [DMF] and then 793 mg (6 mmol) of a benzenethiol sodium salt was added portionwise under ice cooling. The mixture was stirred at room temperature for 2 hours. After dilution with tert-butyl methyl ether, the mixture was washed sequentially with water (three times) and saturated NaCl solution, dried over anhydrous MgSO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 0.4 g of phenyl 2-methyl-N-phenyl-3-(phenylthio)-2-propenimidothioate (hereinafter referred to as the present compound 1).

後処理

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. washAfter dilution with tert-butyl methyl ether, the mixture was washed sequentially with water (three times) and saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1)

出典と根拠

ORDレコード
ord-5716523af6894a709898f1277332beef
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08278473B2

反応ノート

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