Sodium Acetate → ethyl 4-amino-2-propyl-1H-imidazole-5-carboxylate

HRID 1109834노트

반응식

HRID 1109834 반응식
Cl.[C:2](=[NH:7])(OC)[CH2:3][CH3:4].[C:8](O)(=O)C(O)=O.[NH2:14][CH:15]([C:21]#[N:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])(=O)C.[Na+]>C(O)C>[NH2:22][C:21]1[N:7]=[C:2]([CH2:3][CH2:4][CH3:8])[NH:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

참가 물질

5

반응물 3

HCID 517045Sodium AcetateHCID 6917117Ethyl 2-amino-2-cyanoacetate oxalateHCID 12657463Methyl propanimidate--hydrogen chloride (1/1)

생성물 1

HCID 20093493ethyl 4-amino-2-propyl-1H-imidazole-5-carboxylate수율 74.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of methyl propionimidate hydrochloride (4.8 g), ethyl 2-amino-2-cyanoacetate oxalate (4.0 g), anhydrous sodium acetate (9.1 g), and absolute ethanol (75 mL) was stirred at room temperature for 18 hours. Solids were removed by filtration and the filtrate was evaporated. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated NaCl, dried over MgSo4, and evaporated. Flash chromatography on silica gel, eluting with a gradient of dichloromethane-ethyl acetate (75:25) to ethyl acetate gives the title compound (2.7 g) as a pale yellow solid, mp 111°-114° C.; MS (DEI) 211 (m).

후처리

  1. customSolids were removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was washed with saturated NaCl
  5. customdried over MgSo4
  6. customevaporated
  7. washFlash chromatography on silica gel, eluting with a gradient of dichloromethane-ethyl acetate (75:25) to ethyl acetate

출처 및 근거

ORD 기록
ord-72ad30619c8a4f8fb28ad3a900bd689e
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05322950

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