Sulfuric Acid → 2-Amino-4,6-Dinitrotoluene

HRID 1283963

反応式

HRID 1283963 の反応式
OS(O)(=O)=O.O=S(=O)=O.S(=O)(=O)(O)O.[N+:15]([C:18]1[C:19]([CH3:30])=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)C(O)=O)([O-:17])=[O:16].[N-:31]=[N+]=[N-].[Na+]>C(OCC)(=O)C.C(Cl)(Cl)Cl>[N+:15]([C:18]1[C:19]([CH3:30])=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[NH2:31])([O-:17])=[O:16]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 24681Fuming sulfuric acidHCID 33557Sodium AzideHCID 988242-Methyl-3,5-dinitrobenzoic acid

生成物 1

HCID 371822-Amino-4,6-Dinitrotoluene収率 86%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

Chloroform (38 ml.) was added carefully to a stirred mixture of oleum (16.9 ml.: 20% free sulphur trioxide) and concentrated sulphuric acid (3.8 ml.) followed by 3,5-dinitro-2-methylbenzoic acid (10.0 g.). The mixture was warmed to 45°C. and sodium azide (3.28 g.) was added in small portions over 20 minutes, the temperature of the reaction mixture being kept between 45° and 50°C. by means of intermittent cooling. After the addition was complete, the mixture was stirred and heated under reflux for 1 hour on the steam bath and then the chloroform was removed by decantation and the residue was poured into ice-water (300 ml.). The yellow precipitate was filtered off, washed with water and dried, to give crude 3,5-dinitro-2-methylaniline (8.8 g.), m.p. 169°-171°C. The crude product was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and then with water and the solvent was removed in vacuo. Trituration with petroleum ether (b.p. 40°-60°C.) gave 3,5-dinitro-2-methylaniline (7.5 g.), m.p. 172.5°-174.5°C.

後処理

  1. custombeing kept between 45° and 50°C. by means of intermittent cooling
  2. additionAfter the addition
  3. temperatureheated
  4. temperatureunder reflux for 1 hour on the steam bath
  5. customthe chloroform was removed by decantation
  6. additionthe residue was poured into ice-water (300 ml.)
  7. filtrationThe yellow precipitate was filtered off
  8. washwashed with water
  9. customdried
  10. customto give crude 3,5-dinitro-2-methylaniline (8.8 g.), m.p. 169°-171°C
  11. washwashed with saturated aqueous sodium bicarbonate solution
  12. customwith water and the solvent was removed in vacuo

出典と根拠

ORDレコード
ord-adc07a7c285c4fa1a5e7516989145b0f
出典データセット
uspto-grants-1976_08
特許番号
US03976786

関連ノート

読み込み中…