碘化钾 → 2,2-dimethyl-6-iodo-7-nitro-2H-benzo[b]pyran

HRID 223353

反应方程式

HRID 223353 反应方程式
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

参与物

9

反应物 4

HCID 4875碘化钾HCID 82157亚硝基硫酸HCID 132228932,2-Dimethyl-7-nitro-2H-chromen-6-amineHCID 23668193亚硝酸钠

产物 1

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

试剂、催化剂与溶剂 4

HCID 176醋酸溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次HCID 1118四氧化硫溶剂2 次HCID 1140甲苯溶剂

反应条件

温度
8 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-6447c8afb02b4facb2a1934151259adf
来源数据集
uspto-grants-1982_10
专利号
US04353906

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