Potassium Carbonate → 4-(2,5-Dichlorophenylthio)-3-nitrobenzonitrile

HRID 1184372ノート

反応式

HRID 1184372 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].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[SH:21].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([Cl: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

5

反応物 3

HCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 799652,5-Dichlorobenzenethiol

生成物 1

HCID 595489374-(2,5-Dichlorophenylthio)-3-nitrobenzonitrile収率 300.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-chloro-3-nitrobenzonitrile (10.0 g, 54.77 mmol) in THF (300 mL) was added 2,5-dichlorobenzenethiol (19.6 g, 12.108 mmol) and K2CO3 (37.8 g, 273.85 mmol). The reaction mixture was refluxed for 48 hrs. The solid was filtered and washed with copious amounts of EtOAc. The filtrate was washed sequentially with saturated NaHCO3, H2O, and saturated NaCl solution, dried over MgSO4, filtered, and evaporated in vacuo. The resulting solid was then triturated with DCM and hexanes, and filtered to yield compound 27 as a yellow solid (11.823 g, 91.0% HPLC purity, 66.4% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.82 (d, J=2 Hz, 1H), 8.00 (m, 3H), 7.80 (d, J=9 Hz, 1H), 7.75 (dd, J1=3 Hz, J2=9 Hz, 1H), 6.97 (d, J=9 Hz, 2H).

後処理

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. filtrationThe solid was filtered
  3. washwashed with copious amounts of EtOAc
  4. washThe filtrate was washed sequentially with saturated NaHCO3, H2O, and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting solid was then triturated with DCM and hexanes
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-5bda9aa1cd2742509a7b69d6be82375b
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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