1-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dione → HCID 178457568, compound

HRID 2212113Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[O:15])[N:11]=[C:10]2SC)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:18]([O:25][C:26]([NH:28][C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[NH:30])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12](=[O:15])[NH:11][C:10]2=[N:30][C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[N:28][C:26]([O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:27])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To the solution of the crude dione 15 (0.10 g, 0.346 mmol) in 25 ml of dry CHCl3 was added N-(benzyloxycarbonyl)-N′-isopropylguanidine (16) (0.122 g, 0.519 mmol) at room temperature. The reaction mixture was heated at 50° C. for 18 hours and then quenched with water. The mixture was extracted with chloroform and dried over Na2SO4. The CHCl3 was removed in vacuo and the crude product was recrystallized from hexanes/CHCl3 to yield compound 4d as light yellow crystals (51 mg, 0.11 mmol, 31%), mp 211° C. 1H NMR (300 MHz, CDCl3): δ 7.54–7.51(m, 2H), 7.41 (s, 5H), 7.25 (dd, J=8.6 and 2.4 Hz, 1H), 5.25 (s, 2H), 4.12 (m, 1H), 2.46 (d, J=6.6 Hz, 6H). 13C NMR: δ 170.83, 155.86, 153.87, 133.89, 132.56, 132.19, 131.22, 130.42, 129.21, 128.93, 128.65, 128.61, 125.60, 69.24, 45.25, 22.28. MS (m/z): 476 (M+), 370, 316, 314, 236. Anal. (C21H19Cl2N5O4) C, H, Cl, N.

Workup

customquenched with water
extractionThe mixture was extracted with chloroform
dry with materialdried over Na2SO4
customThe CHCl3 was removed in vacuo
customthe crude product was recrystallized from hexanes/CHCl3

Sources & evidence

ORD record: ord-56c7c5c73edb422ba351c0bdea064b98
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101902B2

Reaction notes

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