Hexane → 2-[2-(Benzenesulfonyl)-ethylsulfanyl]-3-nitropyridine

HRID 888259

반응식

HRID 888259 반응식
CC([O-])(C)C.[K+].[C:7]1([S:13]([CH2:16][CH2:17][SH:18])(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=1.CCCCCC>CN(C=O)C.[Cl-].[Na+].O>[C:7]1([S:13]([CH2:16][CH2:17][S:18][C:20]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][N:21]=2)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

7

반응물 4

HCID 8058HexaneHCID 796132-Chloro-3-nitropyridineHCID 4470932-(Phenylsulfonyl)ethanethiolHCID 23665647Potassium tert-butoxide

생성물 1

HCID 671337572-[2-(Benzenesulfonyl)-ethylsulfanyl]-3-nitropyridine수율 46%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

1.8 g (16.0 mmol) potassium tert-butylate were added to a solution of 3.0 g (14.8 mmol) 2-(phenylsulfonyl)ethanethiol in DMF (35 ml) and the mixture was stirred for 30 min at room temperature. Then 2.5 g (15.8 mmol) 2-chloro-3-nitropyridine were added and the mixture was stirred for a further 1 h at RT. Then it was diluted with a brine/EE mixture (1:1 vv) and stirred for a further 30 min at RT. Then the organic phase was separated off, washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 6:1) of the residue yielded 2.2 g (6.8 mmol, 46%) 2-[2-(benzenesulfonyl)-ethylsulfanyl]-3-nitropyridine.

후처리

  1. stirringthe mixture was stirred for a further 1 h at RT
  2. stirringstirred for a further 30 min at RT
  3. customThen the organic phase was separated off
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum

출처 및 근거

ORD 기록
ord-6cd212b40b0f4f10b0d04144f712bace
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247573B2

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