1-Isopropyl-2-methylsulfanyl-1H-imidazole-4,5-dione → HCID 178456566, compound

HRID 2212109Notes

Reaction equation

HRID 2212109 reaction equation
[CH:1]([N:4]1[C:8](=[O:9])[C:7](=[O:10])[N:6]=[C:5]1SC)([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]([NH2:24])=[NH:23])[CH:17]=[CH:18][C:19]=1[Cl:20]>C(Cl)(Cl)Cl>[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]([N:24]=[C:5]2[NH:6][C:7](=[O:10])[C:8](=[O:9])[N:4]2[CH:1]([CH3:3])[CH3:2])=[NH:23])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

4

Reactant 2

HCID 116655211-Isopropyl-2-methylsulfanyl-1H-imidazole-4,5-dioneHCID 178512504HCID 178512504, compound

Product 1

HCID 178456566HCID 178456566, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To the solution of dione 11 (0.712 g, 3.83 mmol) in 80 ml of dry CHCl3 was added guanidine 14 (0.74 g, 3.64 mmol) and the reaction mixture was heated in an oil-bath at 50° C. for 16 hours. The solid precipitates were collected, washed sequentially with H2O, CH3OH and CHCl3 to afford the compound 3 as a light yellow solid (0.497 g, 40%). mp 233° C. 1H NMR (600 MHz, DMSO-d6): δ 7.77 (d, J=2.2 Hz, 1H), 7.68 (d, J=8.6 Hz, 1H), 7.31 (dd, J=8.6 and 2.2 Hz, 1H), 4.38 (m, 1H), 1.33 (d, J=6.7 Hz, 6H). 13C NMR: δ 172.24, 170.65, 162.14, 160.08, 132.13, 131.76, 126.96, 125.00, 44.44, 20.54. IR: 3277, 3140, 1752, 1725, 1553, 1464, 1317, 996, 808, 754 cm−1. Anal. (C13H13Cl2N5O2): C, 45.63; H, 3.83; N, 19.94. Found: C, 45.40; H, 3.71; N, 19.94.

Workup

  1. customThe solid precipitates
  2. customwere collected
  3. washwashed sequentially with H2O, CH3OH and CHCl3

Sources & evidence

ORD record
ord-b91beebbbd2c4820ad4c3520ce217682
Source dataset
uspto-grants-2006_09
Patent number
US07101902B2

Reaction notes

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