O-Toluidine → 3-Aminopyrazine-2carboxylic acid o-toluamide

HRID 430513

反応式

HRID 430513 の反応式
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.N[C:12]1[C:13](C)=[CH:14]C=[CH:16][CH:17]=1.Cl.C[N:21](C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:13]1([CH3:14])[C:3]([C:8]([NH2:21])=[O:10])=[CH:2][CH:16]=[CH:17][CH:12]=1.[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1

参加物

6

反応物 3

HCID 7242O-ToluidineHCID 726563-Amino-2-pyrazinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 697096873-Aminopyrazine-2carboxylic acid o-toluamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-aminopyrazine carboxylic acid (5.0 g, 35.94 mmol), methylene chloride (110 mL), 4-dimethylaminopyridine (10.98 g, 89.85 mmol), o-toluidine (4.22 mL, 39.53 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.27 g, 43.13 mmol) was stirred overnight at ambient temperature. The solvent was removed and the residue was diluted with ethyl acetate. This organic phase was extracted with 1N lithium chloride (LiCl), water, and brine, dried over calcium sulfate and concentrated. The residue was flash chromatographed on silica gel (2.75×4 inches) with elution proceeding as follows: hexane (300 mL), nil; 20% ethyl acetate/hexane (500 mL), unweighed recovered o-toluidine; 20% ethyl acetate/hexane (1000 mL) and 30% ethyl acetate/hexane (2000 mL), 4.79 g (58%) of 3-aminopyrazine-2-carboxylic acid o-toluamide as a yellow crystalline solid.

後処理

  1. customThe solvent was removed
  2. additionthe residue was diluted with ethyl acetate
  3. extractionThis organic phase was extracted with 1N lithium chloride (LiCl), water, and brine
  4. dry with materialdried over calcium sulfate
  5. concentrationconcentrated
  6. customchromatographed on silica gel (2.75×4 inches) with elution proceeding
  7. custom20% ethyl acetate/hexane (500 mL), unweighed recovered o-toluidine

出典と根拠

ORDレコード
ord-30b50b024d454e2f9097c902eda62b64
出典データセット
uspto-grants-2001_11
特許番号
US06323208B1

関連ノート

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