Water → 4-Dimethylthiocarbamoyloxy-2,3-difluoro-5-nitrobenzoic acid methyl ester

HRID 992394Notes

Reaction equation

[F:1][C:2]1[C:11]([F:12])=[C:10]([OH:13])[C:9]([N+:14]([O-:16])=[O:15])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:23][N:24]([CH3:28])[C:25](Cl)=[S:26].O>CN(C)C=O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[C:10]([O:13][C:25](=[S:26])[N:24]([CH3:28])[CH3:23])=[C:11]([F:12])[C:2]=1[F:1]

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of methyl 2,3-difluoro-4-hydroxy-5-nitrobenzoate in N,N-dimethylformamide is treated with one molar equivalent of cesium carbonate and warmed to 85° C. for 30 minutes. The stirring mixture is then treated dropwise rapidly with a solution comprised of a slight excess of N,N-dimethylthiocarbamoyl chloride in N,N-dimethylformamide. The reaction mixture is stirred at room temperature for one hour, or may be warmed over a steam bath for one hour. The mixture is then poured into water and extracted with ethyl acetate. The organic phase is washed with 5% aqueous sodium hydroxide, water, and brine, and is then dried with a drying agent like magnesium sulfate of sodium sulfate. The solvent is then removed in vacuo to give a crude product. The compound is purified by ordinary methods such as chromatography or crystallization from an appropriate solvent.

Workup

additionThe stirring mixture is then treated dropwise rapidly with a solution
temperaturemay be warmed over a steam bath for one hour
extractionextracted with ethyl acetate
washThe organic phase is washed with 5% aqueous sodium hydroxide, water, and brine
dry with materialis then dried with a drying agent like magnesium sulfate of sodium sulfate
customThe solvent is then removed in vacuo

Sources & evidence

ORD record: ord-c0fcab122b1e4cd19c608616b1ef6b07
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06469004B1

Reaction notes

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