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Sodium hydride → 4-((4'-Fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methoxy)-3-nitrobenzenesulfonamide

HRID 2040310
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인쇄 미리보기

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HRID 2040310 반응식
[F:1][C:2]1([CH2:16][OH:17])[CH2:7][CH2:6][C:5]2([O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[O:8]2)[CH2:4][CH2:3]1.[H-].[Na+].F[C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][C:22]=1[N+:31]([O-:33])=[O:32].[NH4+].[Cl-]>CN(C)C=O>[F:1][C:2]1([CH2:16][O:17][C:21]2[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][C:22]=2[N+:31]([O-:33])=[O:32])[CH2:3][CH2:4][C:5]2([O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11]2)[CH2:6][CH2:7]1
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반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 167824874-Fluoro-3-nitrobenzenesulfonamideHCID 67126697(4'-Fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methanol

생성물 1

HCID 671271814-((4'-Fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methoxy)-3-nitrobenzenesulfonamide

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of EXAMPLE 350C (495 mg) in N,N-dimethylformamide (6 mL) was added NaH (65% in mineral oil, 320 mg). The mixture was stirred for 30 minutes, and then 4-fluoro-3-nitrobenzenesulfonamide (457 mg) was added. The mixture was stirred overnight. The mixture was poured over aqueous NH4Cl and extracted with ethyl acetate (300 mL). The combined organic layers were washed with water, brine and dried over Na2SO4. After filtration and evaporation of the solvent, the residue was loaded on a silica gel cartridge and was eluted with 30% ethyl acetate in hexane to provide the title compound.

후처리

  1. stirringThe mixture was stirred overnight
  2. extractionextracted with ethyl acetate (300 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of the solvent
  6. washwas eluted with 30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-c9c1ba6945e244889f9628a73af29da2
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08580794B2

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