Sodium Hydroxide → HCID 1471779、化合物

HRID 865731ノート

反応式

HRID 865731 の反応式
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=2[C:17]#[N:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=2[C:17]#[N:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 706762HCID 706762、化合物

生成物 1

HCID 1471779HCID 1471779、化合物収率 904.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

To a stirred slurry of 4-nitro-2-cyanophenyl phenyl sulfide (13.3 g, 5.19 mmol) and 100 mL of absolute ethanol was added stannous chloride dihydrate (58.6 g, 26 mmol) in one portion. The mixture was heated to 60° C. where an exothermic reaction caused the solution to strongly reflux. The mixture was allowed to stir at ambient temperature for 30 min., poured onto ice-water and made strongly basic by the addition of 350 mL of 15% NaOH. The mixture was extracted with methylene chloride (4×275 mL), the extracts dried (MgSO4), filtered, and the solvent removed in vacuo to yield an oil which was chromatographed on 300 g of silica gel using a methylene chloride (20%, 40%, 60% 80% and 100%) in hexane gradient. The proper fractions were combined and the solvent removed to yield the 4-amino-2-cyano-phenyl phenyl sulfide (10.62 g, 91%) as a pale yellow solid; mp 73°-75° C. 1H-NMR (300 MHz, CDCl3): 4.01 (s, 2H, NH2), 6.78 (dd 1H, J=8.5, 2.6, aromatic), 6.95 (d, 1H, J=2.6, aromatic), 7.18-7.29 (m, 5H, aromatic), 7.34 (d, 1H, J=8.5, aromatic). MS (CI, CH4): 227(M+1).

後処理

  1. customan exothermic reaction
  2. temperatureto strongly reflux
  3. additionpoured onto ice-water
  4. extractionThe mixture was extracted with methylene chloride (4×275 mL)
  5. dry with materialthe extracts dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customto yield an oil which
  9. customwas chromatographed on 300 g of silica gel using a methylene chloride (20%, 40%, 60% 80% and 100%) in hexane gradient
  10. customthe solvent removed

出典と根拠

ORDレコード
ord-89a9d163c19942b580caf6a36405a152
出典データセット
uspto-grants-1996_10
特許番号
US05567735

反応ノート

読み込み中…