Hydrochloric Acid → 3-nitro-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 574779

반응식

HRID 574779 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23].Cl>O1CCCC1.O>[N+:22]([C:13]1[CH:14]=[C:15]([S:18]([NH2:21])(=[O:19])=[O:20])[CH:16]=[CH:17][C:12]=1[O:8][CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)([O-:24])=[O:23]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

생성물 1

HCID 671264583-nitro-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

(Tetrahydro-2H-pyran-4-yl)methanol (2.0 g) in tetrahydrofuran (20 mL) was treated with 60% NaH (1.377 g). The solution was stirred for 20 minutes at the room temperature. To this solution was added 4-fluoro-3-nitrobenzenesulfonamide (2.84 g) portion-wise. The reaction was stirred for another 2 hours. The mixture was poured into water, neutralized with 10% HCl, and extracted with ethyl acetate thee times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel eluting with 20-60% ethyl acetate in hexanes.

후처리

  1. stirringThe reaction was stirred for another 2 hours
  2. extractionextracted with ethyl acetate thee times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with flash column chromatography on silica gel eluting with 20-60% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-56e5bb748bb847798e355dba7de5cd92
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034875B2

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