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Dimethylformamide → HCID 178504721, 화합물

HRID 2369061
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HRID 2369061 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([CH2:28][C:29]#[N:30])=[N:9]1.[N-:31]=[N+:32]=[N-:33].[Na+].[NH4+].[Cl-].CN(C=O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([CH2:28][C:29]2[NH:33][N:32]=[N:31][N:30]=2)=[N:9]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59633179HCID 59633179, 화합물

생성물 1

HCID 178504721HCID 178504721, 화합물수율 78%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

A mixture of [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]acetonitrile (136 mg, 0.3 mmol), NaN3 (59 mg, 0.9 mmol), NH4Cl (49 mg, 0.9 mmol), and anhydrous DMF (5 mL) was stirred in a sealed vial at 120° C. for 24 h. The mixture was poured into water, and extracted with DCM. The combined extracts were washed with water and brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-80% 20% MeOH/DCM) to give the title compound as a white solid (116 mg, 78%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.85-7.83 (m, 1H), 7.74-7.71 (m, 1H), 7.62-7.46 (m, 5H), 7.22 (d, 1H), 6.8 (d, 1H), 6.66 (s, 1H), 4.52 (s, 2H), 3.08 (s, 3H). MS(ES): 497 [M+H]+.

후처리

  1. extractionextracted with DCM
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography (0-80% 20% MeOH/DCM)

출처 및 근거

ORD 기록
ord-385c29d8a1f841be855a41f790ea7c76
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08703805B2

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