Diisopropylethylamine → N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(3-methyl-butyl)-acetamide

HRID 2214701ノート

反応式

HRID 2214701 の反応式
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:6][NH:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11].[CH3:17][C:18]1([CH3:28])[O:22][C:21](=[CH:23][C:24](Cl)=[O:25])[C:20](=[O:27])[O:19]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CCOCC>[Cl:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:6][N:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[C:24](=[O:25])[CH:23]=[C:21]1[C:20](=[O:27])[O:19][C:18]([CH3:17])([CH3:28])[O:22]1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 17206874(3,4-Dichloro-benzyl)-(3-methyl-butyl)-amine hydrochlorideHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

生成物 1

HCID 69655792N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(3-methyl-butyl)-acetamide収率 100%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred mixture of (3,4-dichloro-benzyl)-(3-methyl-butyl)-amine hydrochloride (283 mg, 1.0 mmol) and (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride (206 mg, 1.08 mmol) in CH2Cl2 (10 mL) at room temperature was added diisopropylethylamine (386 μL, 2.2 mmol). After 30 min, the reaction mixture was diluted with ether (50 mL), washed with dilute aqueous HCl (1×5 mL), water (1×10 mL), and saturated aq. NaCl (1×5 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give viscous yellow oil. Purification on a Silica gel column using hexanes/ethyl acetate (20–40% EtOAc) as the eluent gave the title compound as a viscous yellow oil (400 mg, 100% yield). 1H NMR (500 MHz, CDCl3) δ: 7.42–7.26 (2H, m), 7.11 (0.67H, d, J=8.2 Hz), 7.01 (0.33H, d, J=8.2 Hz), 6.14 (0.67H, s), 6.00 (0.33H, s), 4.56 (1.34H, s), 4.52 (0.66H, s), 3.39–3.36 (0.67H, m), 3.29–3.26 (1.33H, m), 1.74 (4H, s), 1.70 (2H, s), 1.59–1.50 (1H, m), 1.47–1.42 (2H, m), 0.90–0.88 (6H, m). MS calcd for C19H24Cl2NO4 (M+H): 400.1. found: 400.07.

後処理

  1. washwashed with dilute aqueous HCl (1×5 mL), water (1×10 mL), and saturated aq. NaCl (1×5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give viscous yellow oil
  6. customPurification on a Silica gel column

出典と根拠

ORDレコード
ord-012ed587142f4c6485b1ff230e9c6344
出典データセット
uspto-grants-2006_09
特許番号
US07109186B2

反応ノート

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