Sodium Thiosulfate → 1-Amino-N-phenyl-1H-imidazole-2-carboxamide

HRID 524988노트

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HRID 524988 반응식
[H-].[Na+].[C:3]1([NH:9][C:10]([C:12]2[NH:13][CH:14]=[CH:15][N:16]=2)=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)(=O)[NH2:24])C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[NH2:24][N:16]1[CH:15]=[CH:14][N:13]=[C:12]1[C:10]([NH:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:11]

참가 물질

6

반응물 4

HCID 24477Sodium ThiosulfateHCID 24758Sodium hydrideHCID 853560DiphenylphosphinamideHCID 2822525N-phenyl-1H-imidazole-2-carboxamide

생성물 1

HCID 211043521-Amino-N-phenyl-1H-imidazole-2-carboxamide수율 76%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

0.430 g (10.75 mmol) of sodium hydride (60% dispersion in mineral oil) was added to a 0° C. cooled solution of N-phenyl-1H-imidazole-2-carboxamide (1.55 g, 8.27 mmol) in DMF (50 mL). The mixture was stirred at 0° C. for 30 minutes and 2.70 g (11.57 mmol) of DPPONH2 (P,P-diphenylphosphinic amide, available from Sigma Aldrich®, cat. no. 5994-87-6) were added portionwise. A thick suspension formed and additional 100 mL of DMF were added. The mixture was stirred at room temperature for 3 hours and then it was poured into 150 mL of a saturated aqueous solution of sodium thiosulphate and extracted with ethyl acetate. The combined organic layer was dried over sodium sulphate, filtered and concentrated. The crude product was purified by flash chromatography (20% to 40% AcOEt/Hexanes) to yield 1.27 g (76% yield) of the title compound as a pale yellow solid.

후처리

  1. addition5994-87-6) were added portionwise
  2. customA thick suspension formed
  3. stirringThe mixture was stirred at room temperature for 3 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (20% to 40% AcOEt/Hexanes)

출처 및 근거

ORD 기록
ord-d0cc1334dd974c8cafb4870783af19a5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340547B2

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