Methyl iodide → methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide

HRID 1803103Notes

Reaction equation

[I:1][CH3:2].[Cl:3][C:4]1[N:5]=[CH:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH2:18])=[S:17])=[CH:11][C:10]=2[O:19][CH3:20])[CH:8]=1>C(O)C>[IH:1].[Cl:3][C:4]1[N:5]=[CH:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([S:17][CH3:2])=[NH:18])=[CH:11][C:10]=2[O:19][CH3:20])[CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Step A (5): Iodomethane (0.890 mL, 14.3 mmol) was added to a solution of 1-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)thiourea (3.85 g, 13.6 mmol) in absolute ethanol (100 mL). The resulting mixture was heated at 70° C. for 3 h. After cooling to rt, the reaction was concentrated in vacuo. The residual volatiles were removed in vacuo to afford methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide (6.32 g, 109% yield) as a white solid. LC-MS (M+H)+ 297.1. 1H NMR (500 MHz, methanol-d4) δ ppm 7.86 (d, J=1.22 Hz, 1 H) 7.55 (d, J=8.24 Hz, 1 H) 7.40 (d, J=1.22 Hz, 1 H) 7.28 (d, J=2.14 Hz, 1 H) 7.08 (dd, J=8.39, 2.29 Hz, 1 H) 3.94 (s, 3 H) 2.76 (s, 3 H).

Workup

temperatureAfter cooling to rt
concentrationthe reaction was concentrated in vacuo
customThe residual volatiles were removed in vacuo

Sources & evidence

ORD record: ord-a608ccb20498462480a199dcf429a18b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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