Hydrochloric Acid → HCID 18759320, compound

HRID 1280381Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].F[C:17]1[CH:22]=[C:21]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]([CH3:34])[C:24]2=[O:35])[C:20]([F:36])=[CH:19][C:18]=1[N+:37]([O-:39])=[O:38].Cl>CN(C)C=O>[F:36][C:20]1[C:21]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:32])([F:31])[F:33])[N:25]([CH3:34])[C:24]2=[O:35])=[CH:22][C:17]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[C:18]([N+:37]([O-:39])=[O:38])[CH:19]=1

Participants

Conditions

Temperature: 65 °C

Procedure

The mixture of 3.53 g of 3-methoxyphenol, 5.12 g of anhydrous potassium carbonate, 10 g of 2,5-difluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzen (described above, produced in Intermediate Production Example 4) and 40 ml of N,N-dimethylformamide was stirred at 60 to 70° C. for 2 hours. The reaction mixture was poured into the mixture of aqueous hydrochloric acid solution and ice water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 4.17 g of 5-fluoro-2-(3-methoxyphenoxy)-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-fa5a099ca9e24d31a4c94106b47d8f58
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451740B2

Reaction notes

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