Hydrochloric Acid → HCID 19985679, 화합물

HRID 528793

반응식

HRID 528793 반응식
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([OH:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2.N([O-])=O.[Na+].[ClH:20]>O.[NH4+].[Cl-].Cl[Cu].[Cu]>[Cl:20][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([OH:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2

참가 물질

8

반응물 3

HCID 313Hydrochloric Acid2회HCID 8386Cleve's acidHCID 23668193Sodium Nitrite

생성물 1

HCID 19985679HCID 19985679, 화합물수율 65%

시약·촉매·용매 4

HCID 23978Copper촉매HCID 62652Cuprous chloride촉매HCID 962Water용매2회HCID 25517Ammonium Chloride용매

반응 조건

온도
0 °C

실험 절차

A solution of 8-amino-2-naphthalenesulfonic acid (Aldrich, 1.00 g, 4.48 mmol) in water (3.0 mL) and conc. HCl (7.0 mL) was cooled to 0° C. A solution of NaNO2 (143 μL, 4.48 mmol) in water (3.0 mL) was added dropwise while maintaining the temperature below 5° C. The reaction mixture was stirred at 0° C. for 1 h. In a separate flask, CuCl (214 μL, 8.96 mmol) was dissolved in conc. HCl (7.0 mL) and the solution was cooled to 0° C. The copper solution was added to the diazonium solution at 0° C. in portions to control the gas evolution. The reaction mixture was allowed to stir at 0° C. for 1 h and then at room temperature for 12 h. The reaction mixture was then diluted with 10% aq. NH4Cl solution and extracted with EtOAc (3×). The combined organic extracts were washed again with aq. 10% NH4Cl solution, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (740 mg, 65%). 1H NMR (DMSO-d6) δ 8.43 (s, 1H), 7.95 (dd, J=17.1, 8.5 Hz, 2H), 7.80 (dd, J=8.4, 1.5 Hz, 1H), 7.71 (dd, J=7.5, 1.1 Hz, 1H), 7.57-7.45 (m, 1H); MS(ESI−) m/z 241.2 (M−H)−.

후처리

  1. temperaturewhile maintaining the temperature below 5° C
  2. temperaturethe solution was cooled to 0° C
  3. stirringto stir at 0° C. for 1 h
  4. waitat room temperature for 12 h
  5. extractionextracted with EtOAc (3×)
  6. washThe combined organic extracts were washed again with aq. 10% NH4Cl solution
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ae77befae3fd462b86b6388918474de7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346795B2

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