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3-fluoro-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide → 3-Hydroxy-N-(4-Methoxybenzyl)-4-Nitro-N-(Thiazol-2-Yl)Benzenesulfonamide

HRID 528571
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HRID 528571 반응식
F[C:2]1[CH:3]=[C:4]([S:11]([N:14]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[O:29]([Si](C)(C)C)[Na]>C1COCC1>[OH:29][C:2]1[CH:3]=[C:4]([S:11]([N:14]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]
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참가 물질

4

반응물 2

HCID 897613943-fluoro-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamideHCID 178504319CID 87414

생성물 1

HCID 897614343-Hydroxy-N-(4-Methoxybenzyl)-4-Nitro-N-(Thiazol-2-Yl)Benzenesulfonamide수율 103%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
25 °C

실험 절차

To a solution of 3-fluoro-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide (9.0 g, 21.2 mmol) in THF (80 mL) was added a THF solution of NaOSi(Me)3 (4.76 g, 42.5 mmoles, 1 M, Aldrich) at 0° C. and the resulting mixture was stirred at 25° C. for 2 h. After completion of the reaction (monitored by TLC), reaction mass was quenched with 1N HCl (70 mL). The organic compound was then extracted with EtOAc, washed with water, dried over sodium sulfate and concentrated to get the 9.20 g of crude material, 3-hydroxy-N-(4-methoxybenzyl)-4-nitro-N-(thiazol-2-yl)benzenesulfonamide as yellow semi-solid which was used for next step as is.

후처리

  1. customAfter completion of the reaction (monitored by TLC), reaction mass
  2. customwas quenched with 1N HCl (70 mL)
  3. extractionThe organic compound was then extracted with EtOAc
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a6fd093c473d45e38aed7090fe8cfa35
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346798B2

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