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

HRID 1442577노트

반응식

HRID 1442577 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-eef6f95d1c034b939db760b8954146e4
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659267B2

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