N,N'-Dimethylethylenediamine → Methyl 4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzoate

HRID 1710333Notes

Reaction equation

[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1.I[C:18]1[CH:23]=[C:22](I)[CH:21]=[CH:20][C:19]=1[C:25]([CH3:28])([CH3:27])[CH3:26].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O1CCOCC1>[C:25]([C:19]1[CH:20]=[CH:21][C:22]([N:6]2[CH2:5][CH2:4][N:3]([C:7]3[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=3)[C:2]2=[O:1])=[CH:23][CH:18]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 110 °C

Procedure

Methyl 4-(2-oxoimidazolidin-1-yl)benzoate (220 mg, 1.0 mmole) was mixed with iodo-1-tert-butyl-4-iodobenzene (260 mg, 1.0 mmol), CuI (38 mg, 0.2 mmol), K3PO4 (426 mg, 2 mmol), N,N′-dimethyl ethylenediamine (17 mg, 0.2 mmol) and 1,4-dioxane (5 ml). The mixture was heated at 110° C. with stirring for 12 hours, and the solvent was removed in vacuum. The residue was suspended in dichloromethane and purified on ISCO system (5% methanol in dichloromethane) to give a pure product as a white crystalline (275 mg, 78%): 1H NMR (400 MHz, CDCl3) δ 8.05 (dd, 2H), 7.70 (dd, 2H), 7.36 (dd, 2H), 7.20 (dd, 2H), 4.02 (s, 4H), 3.90 (s, 3H), 1.30 (s, 9H). MS (ESI) m/z: Calculated: 352.18; Observed: 353.10 (M++1).

Workup

customthe solvent was removed in vacuum
custompurified on ISCO system (5% methanol in dichloromethane)
customto give a pure product as a white crystalline (275 mg, 78%)

Sources & evidence

ORD record: ord-dabb1a89e9dd4857a393e4a8d7cfebce
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790707B2

Reaction notes

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