Hydrochloric Acid → HCID 54330522, compound

HRID 1160871Notes

Reaction equation

HRID 1160871 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) is diluted with methanol (50 mL) and sodium methoxide (4.75 mL of 4.25M in methanol, 20.14 mmol) is added. The reaction is heated to reflux under nitrogen and monitored by TLC. After complete conversion, 20 hours, the reaction is allowed to cool to room temperature. The reaction is neutralized with 1N hydrochloric acid (7.5 mL) and diluted with ethyl acetate (150 mL). The two phases are separated and the organic layer is washed with water (75 mL), then brine (75 mL). The organic layer is dried over anhydrous sodium sulfate, concentrated and loaded onto silica gel column. The title compound is purified using flash column chromatography, yielding 4.0 g, or 92%.

Workup

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

Sources & evidence

ORD record
ord-16b007d34820423b869c1d203ab5dde3
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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