Formaldehyde → Diethyl 1H-imidazole-4,5-dicarboxylate

HRID 1028482ノート

反応式

HRID 1028482 の反応式
[CH2:1]([O:3][C:4](=[O:14])[C@@H:5]([C@H:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])O)O)[CH3:2].Br[N:16]1C(C)(C)C(=O)[N:19](Br)[C:17]1=O.C=O.C([O-])(=O)C.[NH4+].[OH-].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[NH:16]1[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:14])=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:19]=[CH:17]1

参加物

8

反応物 5

HCID 712FormaldehydeHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 6993580Diethyl tartrate

生成物 1

HCID 350670Diethyl 1H-imidazole-4,5-dicarboxylate

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of L-tartaric acid diethyl ester (2.0 g) in ethyl acetate (34.2 ml), 1,3-dibromo-5,5-dimethylhydantoin (3.3 g) was added, and the reaction solution was stirred at room temperature for 3 hours. To the reaction solution, acetic acid (17 ml) was added, and subsequently 36% aqueous formaldehyde solution (3.45 ml) was added under ice cooling at the internal temperature of 10° C. or below, followed by addition of ammonium acetate (17.2 g) at an internal temperature of 10° C. or below. The reaction solution was stirred at room temperature for 30 minutes, followed by stirring at 50° C. for 3 hours. To the reaction solution, 5N sodium hydroxide was added, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, and dried over magnesium sulfate. Quantitative analysis of the resulting ethyl acetate solution by HPLC showed that the title compound was not produced. The condition for HPLC analysis was identical with that for Example 5.

後処理

  1. stirringThe reaction solution was stirred at room temperature for 30 minutes
  2. stirringby stirring at 50° C. for 3 hours
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customwas not produced

出典と根拠

ORDレコード
ord-e512cbfe24dc4a7593040cf9a99cb8f7
出典データセット
uspto-grants-2014_05
特許番号
US08735598B2

反応ノート

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