Nonylamine → 5-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-N-nonyl-benzamide

HRID 584012

反応式

HRID 584012 の反応式
[Cl:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10](O)=[O:11].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH2:47]([NH2:56])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]>C(Cl)Cl>[Cl:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([NH:56][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[O:11]

参加物

6

反応物 4

HCID 16215NonylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 223449015-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-benzoic acid

生成物 1

HCID 223448745-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-N-nonyl-benzamide収率 85.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzoic acid (150 mg, 0.42 mmol) in CH2Cl2 (2 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (84 mg, 0.44 mmol) and 1-hydroxybenzotriazole hydrate (77 mg, 0.50 mmol) with stirring at RT. To the resulting yellow solution was added nonylamine (154 μl, 0.84 mmol) at RT. The resulting mixture was stirred 2 h at RT then solvent removed under a dry nitrogen stream. The residue was purified by preparative TLC (5% Et2O, 45% hexanes, 50% CH2Cl2) to give the title compound of Step C (173 mg). MS (APCl+) Calc.: 482.1. Found: 483.2 (M+1).

後処理

  1. stirringThe resulting mixture was stirred 2 h at RT
  2. customsolvent removed under a dry nitrogen
  3. customThe residue was purified by preparative TLC (5% Et2O, 45% hexanes, 50% CH2Cl2)

出典と根拠

ORDレコード
ord-df1caa79889147e7876c78286bacfb1e
出典データセット
uspto-grants-2005_08
特許番号
US06924310B2

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