Sodium Chloride → Methyl 4-[(2-ethoxy-1-methyl-2-oxoethyl)thio]-2-methyl-5-nitrobenzoate

HRID 1942494Notes

Reaction equation

Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[SH:22][CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].[Cl-].[Na+]>CN(C)C=O>[CH2:27]([O:26][C:24](=[O:25])[CH:23]([S:22][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1)[CH3:29])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 4-chloro-2-methyl-5-nitrobenzoate (2.52 g) in N,N-dimethylformamide (20 ml) were added potassium carbonate (3.04 g) and ethyl 2-mercaptopropionate (2.2 g), and the mixture was stirred at 80° C. for 4 hours. After the reaction was complete, to the mixture was added a saturated aqueous sodium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, concentrated under reduced pressure to give methyl 4-[(2-ethoxy-1-methyl-2-oxoethyl)thio]-2-methyl-5-nitrobenzoate (4.0 g). Subsequently, the title compound was obtained in a similar manner to Reference Example 2.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e70aba7b41eb46e3be9735aa1df62a99
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389511B2

Reaction notes

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