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

HRID 2214701Notes

Reaction equation

HRID 2214701 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-012ed587142f4c6485b1ff230e9c6344
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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