Benzoyl chloride → N-[6-Methoxyquinol-5-yl]thiourea

HRID 1418034

反応式

HRID 1418034 の反応式
[S-:1][C:2]#[N:3].[NH4+].C(Cl)(=O)C1C=CC=CC=1.[NH2:14][C:15]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2>CC(C)=O>[CH3:26][O:25][C:24]1[C:15]([NH:14][C:2]([NH2:3])=[S:1])=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[CH:17]2

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 4596716-Methoxyquinolin-5-amine

生成物 1

HCID 85719096N-[6-Methoxyquinol-5-yl]thiourea

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

1.7 g or ammonium thiocyanate are dissolved in 50 ml of acetone, 2.5 ml of benzoyl chloride are then added and the reaction mixture is heated at reflux for 15 minutes. 2.9 g of amine (Compound 14), dissolved in 20 ml of acetone, are added and the reaction mixture is then heated to reflux for 30 minutes. Evaporation is carried out to dryness and the residue is taken up in water and then extracted with ethyl acetate. The residue is deprotected by treatment with 5 ml of 33% ammonia in 10 ml of ethanol at reflux for 2 hours. The precipitate formed is separated off by filtration, the filtrate is evaporated and the residue is triturated with a 75/25 (v/v) ethyl acetate/hexane mixture, to obtain 3.5 g of white powder. 1H NMR (CDCl3): 3.93 (s, 3H, --OCH3), 7.50-7.53 (m, 1H, H3), 7.70 (d, 1H, J=9.5, 1H, H7), 8.00 (d, J=9.5, 1H, H4), 8.08 (d, 1H, H8), 8.75 (d, J=2.5, 1H, H2).

後処理

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 15 minutes
  3. additionare added
  4. temperaturethe reaction mixture is then heated
  5. temperatureto reflux for 30 minutes
  6. customEvaporation
  7. extractionextracted with ethyl acetate
  8. temperatureat reflux for 2 hours
  9. customThe precipitate formed
  10. customis separated off by filtration
  11. customthe filtrate is evaporated
  12. customthe residue is triturated with a 75/25 (v/v) ethyl acetate/hexane mixture

出典と根拠

ORDレコード
ord-90d1851035cf42d0963e7460d8626e75
出典データセット
uspto-grants-1999_03
特許番号
US05880135

関連ノート

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