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Acetic Anhydride → 3-cyano-4-fluoro-N-(5-fluoro-1,3-thiazol-2-yl)benzenesulfonamide

HRID 1619647
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HRID 1619647 반응식
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[S:15][C@@H:16]([F:20])[C@H:17](O)[N:18]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C(N(CC)CC)C.C(OC(=O)C)(=O)C>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[S:15][C:16]([F:20])=[CH:17][N:18]=2)(=[O:11])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]
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참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 580423263-cyano-4-fluoro-N-[(4S,5R)-5-fluoro-4-hydroxy-4,5-dihydro-1,3-thiazol-2-yl]benzenesulfonamide

생성물 1

HCID 580422733-cyano-4-fluoro-N-(5-fluoro-1,3-thiazol-2-yl)benzenesulfonamide수율 62%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 3-cyano-4-fluoro-N-[(4S,5R)-5-fluoro-4-hydroxy-4,5-dihydro-1,3-thiazol-2-yl]benzenesulfonamide (Preparation 33, 1.42 g, 4.45 mmol) in dichloromethane (150 mL) was added triethylamine (6.20 mL, 44.5 mmol) and acetic anhydride (1.30 mL, 13.8 mL). The reaction mixture was stirred at room temperature under an atmosphere of nitrogen for 18 hours. The mixture was washed with a 2M aqueous solution of hydrogen chloride. The organics were separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The resulting residue was triturated with dichloromethane to afford the title compound as a pale yellow solid (825 mg, 62%).

후처리

  1. washThe mixture was washed with a 2M aqueous solution of hydrogen chloride
  2. customThe organics were separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was triturated with dichloromethane

출처 및 근거

ORD 기록
ord-f68c35a0f3e1464e8d3d20925f0c6118
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08772293B2

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