Hydrochloric Acid → N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-isopropyl-acetamide

HRID 2214699Notes

Reaction equation

HRID 2214699 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:5][NH:6][CH:7]([CH3:9])[CH3:8].Cl.[CH3:15][C:16]1([CH3:26])[O:20][C:19](=[CH:21][C:22](Cl)=[O:23])[C:18](=[O:25])[O:17]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:5][N:6]([CH:7]([CH3:9])[CH3:8])[C:22](=[O:23])[CH:21]=[C:19]1[C:18](=[O:25])[O:17][C:16]([CH3:15])([CH3:26])[O:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 17156247(3,4-Dichloro-benzyl)-isopropyl-amineHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 69656210N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-isopropyl-acetamideYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of (3,4-dichloro-benzyl)-isopropyl-amine; compound hydrochloride (260 mg, 1.024 mmol) and (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride (190 mg, 1.0 mmol) in CH2Cl2 (20 mL) at room temperature was added diisopropylethylamine (350 μL, 2.0 mmol). After 30 min, the reaction mixture was diluted with ethyl acetate (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 (3:2) gave pure product as a viscous yellow oil (372 mg, 93% yield). 1H NMR (500 MHz, CDCl3) δ: 7.41–7.30 (2H, m), 7.11 (0.67H, d, J=10.1 Hz), 7.10 (0.33H, d, J=10.1 Hz), 6.22 (0.67H, s), 5.87 (0.33H, s), 4.87–4.81 (0.33H, m), 4.51 (1.34H, s), 4.47 (0.66H, s), 4.30–4.24 (0.67H, m), 1.73 (4H, s), 1.71 (2H, s), 1.21 (4H, d, J=6.2 Hz), 1.11 (2H, d, J=6.7 Hz). MS calcd for C17H20Cl2NO4 (M+H): 372.24. found: 372.18.

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-97bdc067bd7946c3aa762a10aa95a689
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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