Potassium Carbonate → N-[3-(1H-Pyrazol-1-yl)propyl]-2-nitrobenzenesulfonamide

HRID 1608830ノート

反応式

HRID 1608830 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[NH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH:22]=[CH:21][CH:20]=[N:19]1.C(C)#N.O.C(=O)([O-])[O-].[K+].[K+]>C(C)#N.C(OCC)(=O)C>[N:18]1([CH2:17][CH2:16][CH2:15][NH:14][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH:22]=[CH:21][CH:20]=[N:19]1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 155402-Nitrobenzenesulfonyl chlorideHCID 70231403-(1H-pyrazol-1-yl)propan-1-amineHCID 18373917Acetonitrile--water (1/1)

生成物 1

HCID 22207485N-[3-(1H-Pyrazol-1-yl)propyl]-2-nitrobenzenesulfonamide収率 86.7%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 11.97 g (0.0519 mol) of o-nitrobenzenesulfonyl chloride in 90 ml of cyanomethane was added slowly over several minutes to a cold (7° C.) solution of 10.7 g (0.0540 mol) of N-(3-aminopropyl)-pyrazole in a 3:1 cyanomethane/water solution containing 16.6 g (0.12 mol) of potassium carbonate, under nitrogen. The resulting reaction solution was warmed to room temperature and allowed to react. When the reaction was complete, as determined by thin layer chromatography, the reaction solution was poured into approximately 450 ml of ethyl acetate. The resulting aqueous and organic layers were separated and the organic layer was washed with both an aqueous potassium carbonate solution and an aqueous sodium chloride solution and then reduced to dryness under reduced pressure to provide an oil. This oil was purified using column chromatography (8000 ml of a gradient eluent of from 0 to 5% methanol in methylene chloride). The fractions containing the desired product were combined, reduced to dryness under reduced pressure and then recrystallized from a 1:2 ethyl acetate/diethyl ether solution to provide 13.97 g of the desired subtitled intermediate (m.p. 105°109° C.).

後処理

  1. customThe resulting reaction solution
  2. customto react
  3. customThe resulting aqueous and organic layers were separated
  4. washthe organic layer was washed with both an aqueous potassium carbonate solution
  5. customto provide an oil
  6. customThis oil was purified
  7. additionThe fractions containing the desired product
  8. customrecrystallized from a 1:2 ethyl acetate/diethyl ether solution

出典と根拠

ORDレコード
ord-31cebb0079a94f2ea5d37b90083c7f8c
出典データセット
uspto-grants-1995_03
特許番号
US05397798

反応ノート

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