Water → 2-Phenacylsulfanylacetonitrile

HRID 2396122

反応式

HRID 2396122 の反応式
[SH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].Cl[CH2:12][C:13]#[N:14].C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1>[CH2:2]([S:1][CH2:12][C:13]#[N:14])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

参加物

6

反応物 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 110736092-Mercapto-1-phenylethanone

生成物 1

HCID 3350192-Phenacylsulfanylacetonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Part A. A mixture of 2-mercaptoacetophenone (6.96 g, 45.7 mmol), chloroacetonitrile (3.00 mL, 47.4 mmol), and potassium carbonate (7.21 g, 52.2 mmol) in tetrahydrofuran (100 mL) was stirred at ambient temperature for 12 hours. The mixture was poured into water (400 mL), and this was extracted with ethyl acetate (400 mL), then methylene chloride (400 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane) to afford the product, phenacylthio-acetonitrile, as a pale pink oil (7.51 g, 39.3 mmol, 86%). 1H NMR (CDCl3): δ 7.96 (2H, dd, J=8.0, 1.1 Hz); 7.65-7.56(1H, m); 7.50 (2H, t, J=7.7 Hz); 4.13 (2H, s); 3.45 (2H, s). Mass spectrum (NH3 -CI/DDIP): m/z 210 (21%); 209 (100%); 192 (2%); 170 (1%); 139 (1%).

後処理

  1. extractionthis was extracted with ethyl acetate (400 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-bd946bbe75f640f6a8f36f2f1196fd12
出典データセット
uspto-grants-1996_02
特許番号
US05491152

関連ノート

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