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

HRID 77754

反応式

HRID 77754 の反応式
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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6fb4a07699894e098ba180e9330902a7
出典データセット
uspto-grants-2014_09
特許番号
US08841336B2

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