5-Aminopyridine-2-carbonitrile → 6-Cyanopyridine-3-sulfonyl chloride

HRID 655610

반응식

HRID 655610 반응식
N[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.N([O-])=O.[Na+].[S:14]([Cl:17])(Cl)=[O:15].[OH2:18]>Cl.O>[C:8]([C:5]1[N:6]=[CH:7][C:2]([S:14]([Cl:17])(=[O:15])=[O:18])=[CH:3][CH:4]=1)#[N:9]

참가 물질

6

반응물 3

HCID 38713955-Aminopyridine-2-carbonitrileHCID 23668193Sodium NitriteHCID 86607486Thionylchloride water

생성물 1

HCID 470031906-Cyanopyridine-3-sulfonyl chloride수율 73.5%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

반응 조건

온도
-5 °C

실험 절차

In parallel, 5-amino-2-cyano pyridine (10 g, 0.084 mol) is dissolved in concentrated HCl (98 ml) and the mixture is cooled to −5° C. To this mixture is added dropwise over a period of 1 h a solution of NaNO2 (8.2 g, 0.118 mol) in water (50 ml), maintaining the reaction temperature between −5° C. and 0° C. This slurry is then added dropwise over a period of 1 h to the above reaction mixture (thionylchloride/water mixture), maintaining the reaction temperature between −5° C. and 0° C. (Note: The diazotized mixture should be also kept at −5° C. through out the addition). As the addition proceeds, a white solid precipitates. When the addition is over, the reaction mixture is stirred for an additional hour. The precipitate is collected by filtration, washed with cold water and dried under vacuum to afford the title compound as light yellow solid (12.5 g, Yield 73.5%). 1H NMR (DMSO-d6:400 MHz) δ 14.49 (1H, s), 8.87 (1H, s), 8.11-8.14 (1H, d), 8.0-8.03 (1H, d); HPLC (max plot) 97% Rt 1.155 min; LCMS: m/z, M+, 202.8.

후처리

  1. temperaturemaintaining the reaction temperature between −5° C. and 0° C
  2. temperaturemaintaining the reaction temperature between −5° C. and 0° C. (Note
  3. additionThe diazotized mixture should be also kept at −5° C. through out the addition)
  4. additionAs the addition proceeds
  5. customa white solid precipitates
  6. additionWhen the addition
  7. filtrationThe precipitate is collected by filtration
  8. washwashed with cold water
  9. customdried under vacuum

출처 및 근거

ORD 기록
ord-5cdb54a342e548f1abc315fbc3be0fdf
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071597B2

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