氨基磺酸 → 5-硝基噻吩-2-甲酸

HRID 59746

反应方程式

HRID 59746 反应方程式
[N+:1]([C:4]1[S:8][C:7]([CH:9]=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(=O)(=O)([OH:13])N.Cl([O-])=O.[Na+].C(OCC)(=O)C>O1CCOCC1.O>[N+:1]([C:4]1[S:8][C:7]([C:9]([OH:13])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

参与物

7

反应物 4

HCID 5987氨基磺酸HCID 8857乙酸乙酯HCID 782815-硝基噻吩-2-甲醛2 次HCID 23668197亚氯酸钠

产物 1

HCID 805915-硝基噻吩-2-甲酸收率 193.9%

试剂、催化剂与溶剂 2

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 312751,4-二氧六环溶剂

反应条件

温度
0 °C

实验过程

A mixture of 5-nitrothiophene-2-carbaldehyde (1.685 g, 10.72 mmol) and sulfamic acid (1.249 g, 12.87 mmol) in dioxane (30 ml) was cooled to 0° C., and a solution of sodium chlorite (1.940 g, 21.44 mmol) in water (14 ml) was added drop-wise. The mixture was allowed to warm to RT and stirred for 2 hours. A second batch of 5-nitrothiophene-2-carbaldehyde (1.966 g, 12.51 mmol) was reacted under the same conditions using the molar ratios described above. The two reaction mixtures were combined and portioned between ethyl acetate and water. The organic layer was extracted twice with 5% NaHCO3 and the organic phase was discarded. The basic aqueous phase was acidified with 2N HCl (pH=2) and extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate; the solvent was removed affording 5-nitrothiophene-2-carboxylic acid (Int. 53) (3.6 g, 20.79 mmol, MS/ESI+173.9 [MH]+).

后处理

  1. temperatureto warm to RT
  2. customThe two reaction mixtures
  3. extractionThe organic layer was extracted twice with 5% NaHCO3
  4. extractionextracted twice with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed

来源与证据

ORD记录
ord-be9da77c97c64c5e89118dacb35a924e
来源数据集
uspto-grants-2016_09
专利号
US09440954B2

关联笔记

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