Hydrochloric Acid → HCID 54330522, compound

HRID 660994Notes

Reaction equation

HRID 660994 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([S:9]C(=O)N(C)C)=[CH:4][C:3]=1[CH3:15].C[O-].[Na+].Cl>CO.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([SH:9])=[CH:4][C:3]=1[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86615984HCID 86615984, compound

Product 1

HCID 54330522HCID 54330522, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dimethyl-thiocarbamic acid S-(4-bromo-3,5-dimethyl-phenyl)ester (5.78 g, 20.14 mmol) was diluted with methanol (50 mL) and to this was added sodium methoxide (4.75 mL of 4.25M in methanol, 20.14 mmol). The reaction was heated to reflux under nitrogen and monitored by TLC. After complete conversion, 20 h., the reaction was allowed to cool to room temperature. The reaction was neutralized with 1N HCl (7.5 mL) and diluted with ethyl acetate (150 mL). The two phases were separated and the organic layer was washed with water (75 mL), then brine (75 mL). The organic layer was then dried over anhydrous sodium sulfate, then concentrated and loaded onto silica gel column. The title compound was purified using flash column chromatography, yielding 4.0 g, or 92%.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux under nitrogen
  3. customAfter complete conversion, 20 h.
  4. customThe two phases were separated
  5. washthe organic layer was washed with water (75 mL)
  6. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe title compound was purified
  9. customyielding 4.0 g, or 92%

Sources & evidence

ORD record
ord-1b7155f93abe424cb4bf57340012e99f
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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