Thiophenol → HCID 706762、化合物

HRID 2292908ノート

反応式

HRID 2292908 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]#[N:12].[K].[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(S)C=CC=CC=1.[OH-].[K+]>CO.CN(C)C=O>[C:14]1([S:20][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[C:11]#[N:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 855042-Chloro-5-nitrobenzonitrileHCID 68683554Benzenethiol, potassium salt

生成物 1

HCID 706762HCID 706762、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
105 °C

実験手順

4-Chloro-3-cyanonitrobenzene (12.5 g, 6.84 mmol) was added portionwise to a stirred N,N-dimethylformamide (50 mL) solution of thiophenol potassium salt [prepared by adding thiophenol (7.1 mL, 6.9 mmol) to a solution of potassium hydroxide (3.84 g, 6.84 mmol) in methanol followed by removal of the methanol in vacuo]. After stirring at 105° C. for 2.5 hours the mixture was poured into ice-water, filtered, the collected solid washed with water, dissolved in 300 mL of refluxing ethanol (charcoal), filtered, treated with 35 mL of water and refrigerated. The resulting pale yellow solid weighed 13.3 g (76%), mp 82°-84° C. 1H-NMR (250 MHz, CDCl3): 6.93 (d, 1H, J=9.0 Hz, aromatic), 7.51-7.62 (m, 5H, aromatic), 8.12(dd, 1H, J=9.2, 2.5 Hz, aromatic), 8.46 (d, 1H, J=2.5 Hz, aromatic). MS (CI, CH4): 257(M+1).

後処理

  1. customprepared
  2. customfollowed by removal of the methanol in vacuo]
  3. additionwas poured into ice-water
  4. filtrationfiltered
  5. washthe collected solid washed with water
  6. dissolutiondissolved in 300 mL of refluxing ethanol (charcoal)
  7. filtrationfiltered
  8. additiontreated with 35 mL of water

出典と根拠

ORDレコード
ord-191b7394784c4b9b84c46c3767904c41
出典データセット
uspto-grants-1997_11
特許番号
US05684198

反応ノート

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