1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Benzoic acid, 2-amino-4-(aminocarbonyl)-, methyl ester

HRID 1442577ノート

反応式

HRID 1442577 の反応式
[NH4+].O[N:3]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH2:24][C:25]1[CH:34]=[C:33]([C:35]([O-:37])=O)[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]>CN(C=O)C>[NH2:24][C:25]1[CH:34]=[C:33]([C:35]([NH2:3])=[O:37])[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]

参加物

5

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21924002HCID 21924002、化合物HCID 220338091-Hydroxybenzotriazole, ammonium salt

生成物 1

HCID 19064836Benzoic acid, 2-amino-4-(aminocarbonyl)-, methyl ester収率 92%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Under ice cooling, 1-hydroxy-1H-benzotriazole ammonium salt (6.86 g, 45.1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.64 g, 45.1 mmol) were added to DMF solution (40 mL) of 1-methyl 2-aminoterephthalate (8.0 g, 41.0 mmol). The mixture was stirred at the same temperature for 1.5 hours and at room temperature for 30 minutes. After ice water was added to the reaction mixture, the precipitated crystals were taken by filtration and washed with water and diethyl ether. The filtrate was neutralized with sodium hydrogencarbonate, which was extracted 4 times with a tetrahydrofuran-ethyl acetate mixture. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was crystallized from water-ethyl acetate to give the title compound (7.32 g, 92%).

後処理

  1. filtrationthe precipitated crystals were taken by filtration
  2. washwashed with water and diethyl ether
  3. extractionwas extracted 4 times with a tetrahydrofuran-ethyl acetate mixture
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from water-ethyl acetate

出典と根拠

ORDレコード
ord-eef6f95d1c034b939db760b8954146e4
出典データセット
uspto-grants-2010_02
特許番号
US07659267B2

反応ノート

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