Ethyl Acetate → 4-(2,5-Dimethylphenylthio)-3-nitrobenzonitrile

HRID 1184369ノート

反応式

HRID 1184369 の反応式
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[SH:21].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C1COCC1>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[S:21][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 776152,5-Xylenethiol

生成物 1

HCID 291067464-(2,5-Dimethylphenylthio)-3-nitrobenzonitrile収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-chloro-3-nitrobenzonitrile (5.4 g, 29.67 mmol) in THF (100 mL) was added 2,5-dimethylthiophenol (4.921 g, 35.60 mmol) and K2CO3 (20.45 g, 148.0 mmol). The reaction was monitored with TLC (25% EtOAc in hexanes). After refluxing for 16 hrs, the reaction was complete. The solid was filtered and washed with copious amounts of EtOAc. The filtrate was washed sequentially with saturated NaHCO3, water, saturated NaCl solution, dried over MgSO4, filtered, and evaporated in vacuo. The resulting solid was then sonicated in hexanes and filtered to yield compound 24 as a yellow/white solid (8.00 g, 97.8% HPLC purity, 95% yield). 1H NMR (500 MHz, DMSO-d6): δ8.77 (d, J=2 Hz, 1H), 7.94 (dd, J1=2 Hz, J2=8 Hz, 1H), 7.46 (s, 1H), 7.41 (d, J=8 Hz, 1H), 7.36 (d, J=8 Hz, 1H), 6.76 (d, J=8 Hz, 1H), 2.32 (s, 3H), 2.23 (s, 3H).

後処理

  1. temperatureAfter refluxing for 16 hrs
  2. filtrationThe solid was filtered
  3. washwashed with copious amounts of EtOAc
  4. washThe filtrate was washed sequentially with saturated NaHCO3, water, saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting solid was then sonicated in hexanes
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-81b46ca2ce3e4ba49ac5258696959a7d
出典データセット
uspto-grants-2014_03
特許番号
US08669247B2

反応ノート

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