Potassium Carbonate → 5-Chloro-4-(4-chloro-2-fluoro-5-(4,6-dimethoxy-2-triazinyloxy)phenyl)-1-difluoromethyl-2-methylimidazole

HRID 380293Notes

Reaction equation

HRID 380293 reaction equation
[Cl:1][C:2]1[N:6]([CH:7]([F:9])[F:8])[C:5]([CH3:10])=[N:4][C:3]=1[C:11]1[CH:16]=[C:15]([OH:17])[C:14]([Cl:18])=[CH:13][C:12]=1[F:19].C(=O)([O-])[O-].[K+].[K+].Cl[N:27]1[N:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[NH:28]1>CN(C)C=O>[Cl:1][C:2]1[N:6]([CH:7]([F:8])[F:9])[C:5]([CH3:10])=[N:4][C:3]=1[C:11]1[CH:16]=[C:15]([O:17][N:27]2[N:28]=[C:29]([O:35][CH3:36])[CH:30]=[C:31]([O:33][CH3:34])[NH:32]2)[C:14]([Cl:18])=[CH:13][C:12]=1[F:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 183295865-Chloro-4-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-difluoromethyl-2-methylimidazoleHCID 221477162-Chloro-4,6-dimethoxy-triazine

Product 1

HCID 184030185-Chloro-4-(4-chloro-2-fluoro-5-(4,6-dimethoxy-2-triazinyloxy)phenyl)-1-difluoromethyl-2-methylimidazoleYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5-Chloro-4-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-difluoromethyl-2-methylimidazole (prepared according to the procedure as described in EP 590,834) (0.31 g, 1 mMol) was dissolved in N,N-dimethylformamide (5 ml). Potassium carbonate (0.17 g, 1.2 mMol) and 2-chloro-4,6-dimethoxytriazine (0.21 g, 1.2 mMol) were added and the suspension stirred at 110° C. for 2 hours under an atmosphere of nitrogen. The mixture was processed and the residue chromatographed on silica gel eluting with methylene chloride:methanol, 98:2, to give the title compound (0.25 g, 55%). 1H NMR (CDCl3, TMS): 2.61 (3H, br s), 4.00 (6H, s), 7.17 (1H, t, J=58.1 Hz), 7.29 (1H, d, J=9.3 Hz), 7.53 (1H, d, J=6.6 Hz).

Workup

  1. customthe residue chromatographed on silica gel eluting with methylene chloride

Sources & evidence

ORD record
ord-f0ba45def0e94097a6cab55486d22adf
Source dataset
uspto-grants-2001_10
Patent number
US06303543B1

Reaction notes

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