1-(3,4-dichlorophenyl)-2-methylsulfanyl-1H-imidazole-4,5-dione → HCID 178512082, compound

HRID 2212108Notes

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].[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]([NH2:29])=[NH:28])[CH:22]=[CH:23][C:24]=1[Cl:25]>C(Cl)(Cl)Cl>[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]([N:29]=[C:10]2[NH:11][C:12](=[O:15])[C:13](=[O:14])[N:9]2[C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[NH:28])[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To the solution of the crude dione 15 (0.551 g, 1.907 mmol) in 25 ml of dry CHCl3 was added N-(3,4-dichlorophenyl)guanidine (14) (0.389 g, 1.907 mmol) at room temperature. The reaction mixture was heated at 50° C. overnight. The solid was collected and washed sequentially with CHCl3 and H2O to afford the compound 19 as a light yellow solid (0.573 g, 1.288 mmol, 68%), mp 220° C. 1H NMR (300 MHz, DMSO-d6): δ 7.75(d, J=8.3 Hz, 1H), 7.69 (s, 1H), 7.55–7.40 (m, 3H), 7.15 (d, 7.9 Hz, 1H); 13C NMR: δ 170.54, 169.33, 160.26, 156.74, 136.75, 132.72, 131.15, 131.00, 130.73, 130.52, 129.64, 128.04. MS (m/z) 444 (MH+), 256, 227, 185. Anal. (C16H9Cl4N5O2) C, H, Cl, N.

Workup

customThe solid was collected
washwashed sequentially with CHCl3 and H2O

Sources & evidence

ORD record: ord-c1fb98ad16ee4fda80e1a06675a7790a
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101902B2

Reaction notes

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