Triethylamine → Methyl 4-[(2-amino-5-iodo-benzoylamino)-methyl]-benzoate

HRID 1062585

Reaktionsgleichung

Reaktionsgleichung von HRID 1062585
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.[NH2:32][C:33]1[CH:41]=[CH:40][C:39]([I:42])=[CH:38][C:34]=1[C:35](O)=[O:36].Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[NH2:32][C:33]1[CH:41]=[CH:40][C:39]([I:42])=[CH:38][C:34]=1[C:35]([NH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=1)=[O:36]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 22281877Methyl 4-[(2-amino-5-iodo-benzoylamino)-methyl]-benzoateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 15 g (74.4 mmol) of methyl 4-(aminomethyl)benzoate hydrochloride, 300 ml of dimethylformamide and 10.3 ml (7.53 g, 74.4 mmol) of triethylamine were added, at room temperature, followed by 10.06 g (74.4 mmol) of 1-hydroxybenzotriazole hydrate, 19.6 g (74.4 mmol) of 2-amino-5-iodobenzoic acid and 14.3 g (74.4 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. After stirring at room temperature overnight, the mixture was concentrated and the residue was dissolved in 300 ml of dichloromethane. The organic phase was washed with 150 ml H2O, 150 ml HCl 1N, and 150 ml H2O, dried over sodium sulfate and concentrated. The residue was recrystallized from 170 ml acetonitrile to afford after filtration 19.6 g of the desired product (yield: 70%).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in 300 ml of dichloromethane
  3. washThe organic phase was washed with 150 ml H2O, 150 ml HCl 1N, and 150 ml H2O
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from 170 ml acetonitrile
  7. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-fc77ddb5ab5549c5b7e3d30e19bd348e
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962922B2

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