N-methyl-2-pyrrolidone → 3-Iodo-N-(2-methoxy-1-methyl-ethyl)-5-nitro-benzamide

HRID 84732

Reaktionsgleichung

Reaktionsgleichung von HRID 84732
CCN=C=NCCCN(C)C.[I:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[C:16]([OH:18])=O.C1C=CC2N(O)N=NC=2C=1.[NH2:35][CH:36]([CH3:40])[CH2:37][O:38][CH3:39].CN1C(=O)CCC1>C(Cl)Cl.CN(C=O)C>[I:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[C:16]([NH:35][CH:36]([CH3:40])[CH2:37][O:38][CH3:39])=[O:18]

Komponenten

8

Edukt 5

HCID 13387N-methyl-2-pyrrolidoneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 805803-Iodo-5-nitrobenzoic acidHCID 123458Methoxyisopropylamine

Produkt 1

HCID 578513193-Iodo-N-(2-methoxy-1-methyl-ethyl)-5-nitro-benzamideAusbeute 27,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

EDCI (7.07 g, 36.9 mmol) was added in one portion to a stirred solution of 3-Iodo-5-nitro-benzoic acid (2.31 g, 24.6 mmol), HOBt (4.985 g, 36.9 mmol), 2-Amino-1-methoxypropane (2.73 ml, 24.6 mmol) and NMP (4.06 ml 36.9 mmol) in CH2Cl2 (120 ml) and DMF (10 ml) at 0° C. The reaction was allowed to warm to room temperature and was stirred over night. The reaction mixture was then washed with 2N NaOH, water, brine, and dried over Na2SO4. Solvent was removed in vacuo to give 2.50 g of 3-Iodo-N-(2-methoxy-1-methyl-ethyl)-5-nitro-benzamide as a yellow solid, MS (M+H)=365. This material was used without further purification.

Aufarbeitung

  1. washThe reaction mixture was then washed with 2N NaOH, water, brine
  2. dry with materialdried over Na2SO4
  3. customSolvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0d9589c7e058451894f1ce443e0d8999
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846945B2

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