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

HRID 84732

반응식

HRID 84732 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-0d9589c7e058451894f1ce443e0d8999
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846945B2

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