Potassium Iodide → 2,2-dimethyl-6-iodo-7-nitro-2H-benzo[b]pyran

HRID 223353

反応式

HRID 223353 の反応式
N[C:2]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:5]2[O:6][C:7]([CH3:11])([CH3:10])[CH:8]=[CH:9][C:4]=2[CH:3]=1.N(OS(=O)(=O)O)=O.N([O-])=O.[Na+].[I-:28].[K+]>C(O)(=O)C.S(=O)(=O)(O)O.O.C1(C)C=CC=CC=1>[CH3:10][C:7]1([CH3:11])[O:6][C:5]2[CH:12]=[C:13]([N+:14]([O-:16])=[O:15])[C:2]([I:28])=[CH:3][C:4]=2[CH:9]=[CH:8]1

参加物

9

反応物 4

HCID 4875Potassium IodideHCID 82157Nitrosylsulfuric acidHCID 132228932,2-Dimethyl-7-nitro-2H-chromen-6-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 153077022,2-dimethyl-6-iodo-7-nitro-2H-benzo[b]pyran収率 39.4%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回HCID 1118Sulfuric Acid溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
8 °C

実験手順

To a cooled solution of 6-amino-2,2-dimethyl-7-nitro-2H-benzo[b]pyran (20.0 g)* in glacial acetic acid (800 ml) was added concentrated sulphuric acid (400 ml) and the solution stirred at 8° C. Nitrosyl sulphuric acid (prepared by dissolving sodium nitrite (6.62 g) in cold concentrated sulphuric acid (200 ml) the mixture being warmed to dissolved the solid then re-cooled to approximately 4° C.) was added keeping the temperature of the reaction mixture below 12° C. The dark, viscous mixture was stirred at approximately 7° C. for a further hour then poured into a cold (approximately 5° C.) solution of potassium iodide (15.27 g) in water (200 ml). Toluene (800 ml) was added to dissolve the resulting precipitate and the mixture stirred in an ice bath for 20 minutes, then at room temperature for 18 hours. The reaction mixture was diluted with water (500 ml), the organic phase was separated, washed with water, dried and evaporated in vacuo to afford the required 2,2-dimethyl-6-iodo-7-nitro-2H-benzo[b]pyran (11.84 g, 39%) as a red gum.

後処理

  1. temperaturebeing warmed
  2. dissolutionto dissolved the solid
  3. temperaturethen re-cooled to approximately 4° C.)
  4. additionwas added
  5. customthe temperature of the reaction mixture below 12° C
  6. stirringThe dark, viscous mixture was stirred at approximately 7° C. for a further hour
  7. dissolutionto dissolve the resulting precipitate
  8. stirringthe mixture stirred in an ice bath for 20 minutes
  9. customthe organic phase was separated
  10. washwashed with water
  11. customdried
  12. customevaporated in vacuo

出典と根拠

ORDレコード
ord-6447c8afb02b4facb2a1934151259adf
出典データセット
uspto-grants-1982_10
特許番号
US04353906

関連ノート

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