Ammonium Hydroxide → 2-Amino-cyclopent[b]pyrazine

HRID 1464631

反応式

HRID 1464631 の反応式
Cl.Cl.[NH2:3][CH2:4][C:5]([NH2:7])=[NH:6].[C:8]1(=O)[CH2:12][CH2:11][CH2:10][C:9]1=O.[NH4+].[OH-]>O.C(O)C.Cl>[NH2:6][C:5]1[NH:7][C:9]2=[CH:10][CH:11]=[CH:12][C:8]2=[N:3][CH:4]=1

参加物

7

反応物 3

HCID 14923Ammonium Hydroxide2 回HCID 5666571,2-CyclopentanedioneHCID 189434792-Aminoethanimidamide dihydrochloride

生成物 1

HCID 190871152-Amino-cyclopent[b]pyrazine

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A solution of aminoacetamidine dihydrochloride (Mengelberg, M. Chem. Ber. 89, 1185 (1956)) (2.4 g, 0.01 mol, 1 equiv.) in H2O (~10 mL) was added dropwise to a cold (0° C.) stirring solution of 1,2-cyclopentanedione (1.0 g, 0.01 mol) in ethanol (8-10 mL). After allowing the reaction mixture to come to room temperature, concentrated NH4OH (aq.) was added slowly until the pH was 8-9. Small amounts of concentrated NH4OH were added as needed in order to maintain a pH of 8-9. When the 1,2-cycopentanedione was no longer visible on TLC (30% EtOAc/hexanes) the reaction mixture was diluted with 5% HCl, washed (3×) with CH2Cl2 and the organic portions discarded. The aqueous portion was made basic with 6N NaOH (aq.), extracted (4×) with CH2Cl2 and the combined extracts dried over sodium sulfate. Concentration of the solution under reduced pressure gave 2-amino-cyclopent[b]pyrazine as a greenish-yellow solid.

後処理

  1. customto come to room temperature
  2. temperatureto maintain a pH of 8-9
  3. washwashed (3×) with CH2Cl2
  4. extractionextracted (4×) with CH2Cl2
  5. dry with materialthe combined extracts dried over sodium sulfate

出典と根拠

ORDレコード
ord-b553f039de38481a8d3207137b1b69d9
出典データセット
uspto-grants-1994_04
特許番号
US05306819

関連ノート

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