Ammonia → 1-(6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-yl)thiourea

HRID 1803164Notes

Reaction equation

HRID 1803164 reaction equation
[NH3:1].[Cl:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][C:11]([N:16]=[C:17]=[S:18])=[CH:10][N:9]=2)[CH:7]=1>>[Cl:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[N:9]=[CH:10][C:11]([NH:16][C:17]([NH2:1])=[S:18])=[CH:12][C:13]=2[O:14][CH3:15])[CH:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 866499162-(4-chloro-1H-imidazol-1-yl)-5-isothiocyanato-3-methoxypyridine

Product 1

HCID 866499171-(6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-yl)thioureaYield 84.2%

Procedure

Step O (4): Methanolic ammonia (2.0 M, 25 mL, 50 mmol) was added to a flask charged with 2-(4-chloro-1H-imidazol-1-yl)-5-isothiocyanato-3-methoxypyridine (2.5 g, 9.37 mmol). After 16 h, the reaction mixture was concentrated in vacuo to afford 1-(6-(4-chloro-1H-imidazol-1-yl)-5-methoxypyridin-3-yl)thiourea (2.24 g, 7.89 mmol, 84% yield). LC-MS (M+H)+ 283.9. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.24 (d, J=1.83 Hz, 1 H) 8.12 (d, J=2.14 Hz, 1 H) 8.09 (d, J=2.14 Hz, 1 H) 7.79-7.82 (m, 1 H) 3.90-3.95 (m, 3 H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ebef9b44b85748f6866559256486b2fd
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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