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

HRID 1109834ノート

反応式

HRID 1109834 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-72ad30619c8a4f8fb28ad3a900bd689e
出典データセット
uspto-grants-1994_06
特許番号
US05322950

反応ノート

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