Acetic Acid → 3-Nitropyridine-2-sulfonyl chloride

HRID 513715

反応式

HRID 513715 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 543288413-Nitropyridine-2-sulfonyl chloride

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ae600ed080864edbab166c47129b72c2
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

関連ノート

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