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

HRID 77754

Reaction equation

HRID 77754 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

HCID 578513193-Iodo-N-(2-methoxy-1-methyl-ethyl)-5-nitro-benzamideYield 27.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6fb4a07699894e098ba180e9330902a7
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Linked notes

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