1-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dione → HCID 178457571, compound

HRID 2212112Notes

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].[CH:18]([NH:21][C:22]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[NH:23])([CH3:20])[CH3:19]>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:23][C:22]([NH:21][CH:18]([CH3:20])[CH3:19])=[N:24][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To the solution of the crude dione 15 (0.7 g, 2.5 mmol) in 25 ml of dry CHCl3 was added N-isopropyl-N′-(tert-butoxycarbonyl)-guanidine (17) (0.5 g, 2.5 mmol). The reaction mixture was heated at 50° C. for 16 hours. The reaction was quenched with water, extracted with chloroform and dried over Na2SO4. The solvent was removed in vacuo and the crude product was purified with a silica gel column and was eluted with 3% EtOAc/CHCl3 to yield 4c as a white solid (0.25 g, 22%), mp 227° C. 1H NMR (300 MHz, CDCl3): δ 7.55 (d, J=2.4 Hz, 1H), 7.53(d, J=8.6 Hz, 1H), 7.27 (dd, J=8.6 and 2.4 Hz, 1H), 4.15 (m, 1H), 1.54 (s, 9H), 1.24 (d, J=6.6 Hz, 6H); 13C NMR: δ 170.50, 168.40, 159.34, 156.09, 153.00, 132.51, 132.09, 131.34, 130.38, 128.62, 125.62, 85.59, 45.05, 29.70, 22.34. IR: 2979, 2930, 1766, 1729, 1532, 1474, 1142, 775, 734 cm−1. MS (m/z): 444 (M++1).

Workup

customThe reaction was quenched with water
extractionextracted with chloroform
dry with materialdried over Na2SO4
customThe solvent was removed in vacuo
customthe crude product was purified with a silica gel column
washwas eluted with 3% EtOAc/CHCl3

Sources & evidence

ORD record: ord-5d9c9f66529740b395741c4a896be2e3
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101902B2

Reaction notes

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