Acetic Acid → 3-Nitropyridine-2-sulfonyl chloride

HRID 513715

반응식

HRID 513715 반응식
CC(O)=O.C(S[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1)C1C=CC=CC=1.[Cl:22]N1C(C)(C)C(=O)N(Cl)C1=O.[S:33](S([O-])=O)([O-:36])(=O)=[O:34].[Na+].[Na+]>C(Cl)Cl.O>[N+:19]([C:18]1[C:13]([S:33]([Cl:22])(=[O:36])=[O:34])=[N:14][CH:15]=[CH:16][CH:17]=1)([O-:21])=[O:20]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 5073002-(Benzylthio)-3-nitropyridineHCID 656671Sodium Pyrosulfite

생성물 1

HCID 543288413-Nitropyridine-2-sulfonyl chloride

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

AcOH (6 ml) and water (12 ml) were added to a solution of 2-benzylsulfanyl-3-nitro-pyridine 437 (3.0 g, 12.2 mmol) in DCM (42 ml) and the mixture was cooled to 0° C. A suspension of 1,3-dichloro-5,5-dimethyl-imidazolidine-2,4-dione (7.20 g, 36.58 mmol) in DCM (24 ml) was added portionwise to the vigorously stirring solution. The mixture was allowed to slowly warm to 25° C. and stirring was continued for 16 h. The mixture was poured into 5% aq. sodium metabisulfite solution (50 ml) and the aqueous phase was extracted with DCM (100 ml). The organic phase was washed with water, sat. NaHCO3 solution and brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (2.7 g) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

후처리

  1. additionwas added portionwise to the vigorously stirring solution
  2. temperatureto slowly warm to 25° C.
  3. extractionthe aqueous phase was extracted with DCM (100 ml)
  4. washThe organic phase was washed with water, sat. NaHCO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ae600ed080864edbab166c47129b72c2
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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