海萝胶 → 4-Acetyl-2-fluorobenzene-1-sulfonamide

HRID 396820

反应方程式

HRID 396820 反应方程式
[C:1]([C:4]1[CH:10]=[CH:9][C:7](N)=[C:6]([F:11])[CH:5]=1)(=[O:3])[CH3:2].Cl.[N+:13]([O-])([O-])=O.[Na+].[S:18](=[O:20])=[O:19]>O.C(O)(=O)C.O.O.[Cu](Cl)Cl>[C:1]([C:4]1[CH:10]=[CH:9][C:7]([S:18]([NH2:13])(=[O:20])=[O:19])=[C:6]([F:11])[CH:5]=1)(=[O:3])[CH3:2]

参与物

8

反应物 4

HCID 313海萝胶HCID 1119二氧化硫HCID 24268硝酸钠HCID 30184634'-氨基-3'-氟苯乙酮

产物 1

HCID 223169644-Acetyl-2-fluorobenzene-1-sulfonamide收率 46.6%

试剂、催化剂与溶剂 3

HCID 61482二水氯化铜催化剂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

实验过程

To a solution of 4-acetyl-2-fluoroaniline (5.0 g, 32.6 mmol, Krueger, G et al., Arzneim Forsch, 34, 11a, 1612 (1984)) in conc-HCl (24.0 mL), sodium nitrate (2.9 g, 42.4 mmol) in water (10 mL) was added at 0° C. After stirring for 1 h, the resultant yellow solution was added slowly to the suspension of copper (II) chloride dihydrate (1.7 g, 9.8 mmol) and sulfur dioxide (10 g, 156 mmol) in acetic acid (25 mL) at 0° C. The mixture was stirred for 30 min at 0° C. and poured into ice water (200 mL) and extracted with CH2Cl2 (80 mL×2). The extracts was cooled to 0°0 C. and 25% aqueous ammonia (70 mL) was added slowly and stirred for 1 h at room temperature. The mixture was concentrated and the residual solid was suspended with ether and collectted by filteration to give the title compound (3.3 g, 46%).

后处理

  1. stirringThe mixture was stirred for 30 min at 0° C.
  2. extractionextracted with CH2Cl2 (80 mL×2)
  3. temperatureThe extracts was cooled to 0°0 C
  4. additionand 25% aqueous ammonia (70 mL) was added slowly
  5. stirringstirred for 1 h at room temperature
  6. concentrationThe mixture was concentrated

来源与证据

ORD记录
ord-d25eb92e784145a1937ff17551df66f6
来源数据集
uspto-grants-2003_08
专利号
US06608095B2

关联笔记

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