Sulfamic Acid → 5-Nitro-2-thenoic acid

HRID 59746

반응식

HRID 59746 반응식
[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]

참가 물질

7

반응물 4

HCID 5987Sulfamic AcidHCID 8857Ethyl AcetateHCID 782815-Nitrothiophene-2-carboxaldehyde2회HCID 23668197Sodium Chlorite

생성물 1

HCID 805915-Nitro-2-thenoic acid수율 193.9%

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

반응 조건

온도
0 °C

실험 절차

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]+).

후처리

  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

출처 및 근거

ORD 기록
ord-be9da77c97c64c5e89118dacb35a924e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440954B2

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