Hydrochloric Acid → Methyl 4-[(2-ethoxy-1,1-dimethyl-2-oxoethyl)thio]-2-methyl-5-nitrobenzoate

HRID 1942492Notes

Reaction equation

HRID 1942492 reaction equation
[SH:1][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+].Br[C:23]([CH3:30])([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].Cl>CN(C)C=O.O>[CH2:27]([O:26][C:24](=[O:25])[C:23]([S:1][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)([CH3:30])[CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 58376194Methyl 4-mercapto-2-methyl-5-nitrobenzoate

Product 1

HCID 67331043Methyl 4-[(2-ethoxy-1,1-dimethyl-2-oxoethyl)thio]-2-methyl-5-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 4-mercapto-2-methyl-5-nitrobenzoate (1.17 g) in N,N-dimethyl-formamide (20 ml) were added potassium carbonate (1.42 g), ethyl 2-bromoisobutyrate, and the mixture was stirred at 80° C. for 4 hours. After the reaction was complete, water and 2N hydrochloric acid were added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, concentrated under reduced pressure. The obtained residue was purified by column chromatography to give a crude product of the title compound (3.56 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-bac5a6ce22aa410483927f81c9f38d0d
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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