2-(2-Nitroimidazol-1-yl)acetic acid → N-(3-methyl-2-butenyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide

HRID 1377389노트

반응식

HRID 1377389 반응식
[N+:1]([C:4]1[N:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.[CH3:26][C:27]([CH3:31])=[CH:28][CH2:29][NH2:30].C([O-])(O)=O.[Na+]>CN(C=O)C.CO.ClCCl>[CH3:26][C:27]([CH3:31])=[CH:28][CH2:29][NH:30][C:10](=[O:12])[CH2:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 3275442-(2-Nitroimidazol-1-yl)acetic acid2회HCID 516892Sodium BicarbonateHCID 5250894Bis-(1H-imidazol-2-YL)-methanone2회HCID 183265643-Methylbut-2-en-1-amine hydrochloride

생성물 1

HCID 18929154N-(3-methyl-2-butenyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 21226129Dichloromethane methanol용매

실험 절차

2-(2-Nitro-1H-imidazol-1-yl)acetic acid (8.6 g, 50 mmol) was dissolved in DMF (50 mL). Carbonyl diimidazole [CDI] (8.7 g, 60 mmol) was added to the solution in small portions. The reaction mixture was stirred under N2 for 15 min. 3,3-Dimethylallylamine hydrochloride was suspended in DMF (50 mL) and stirred with NaHCO3 (4.2 g, 50 mmol). This suspension was added to the CDI and 2-(2-nitro-1H-imidazol-1-yl)acetic acid in DMF solution. The mixture was stirred under N2 atmosphere at room temperature overnight. TLC (silica gel, 10% methanol-dichloromethane) showed one spot with Rf =0.5, indicating completion of the reaction. DMF was evaporated on a rotary evaporator and the residue was triturated with ice-water (125 mL) and filtered. The solid was washed with cold water (3×50 mL) and dried in vacuum to give a white solid. Yield: 7.2 g (61%). mp: 174°-176° C. MS: 254 (M+NH4)+, 238 (M+H)+. 1H NMR (DMSO-d6) δ1.62 and 1.68 [s, 6H, =C(C H3)2 ], 3.68 (t, 2H, C H2CH=), 5.08 (s, 2H, COCH2 -imidazolyl), 5.14 (t, 1H, CH2C H=), 7.19 and 7.62 (s, 2H, 2-nitroimidazolyl- H), 8.37 (t, 1H, HNCO). Anal. Calcd. for C20H32N10O7 : Calcd: C, 50.41; H, 5.92; N, 23.52. Found: C, 50.67; H, 5.97; N 23.38.

후처리

  1. stirringThe mixture was stirred under N2 atmosphere at room temperature overnight
  2. customcompletion of the reaction
  3. customDMF was evaporated on a rotary evaporator
  4. customthe residue was triturated with ice-water (125 mL)
  5. filtrationfiltered
  6. washThe solid was washed with cold water (3×50 mL)
  7. customdried in vacuum
  8. customto give a white solid

출처 및 근거

ORD 기록
ord-bf77609570b540a5b67a6c66beaf582b
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665329

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