Hydrochloric Acid → Methyl (4-ethoxy-3-fluorophenyl)carbamodithioate

HRID 482556

Reaction equation

HRID 482556 reaction equation
[C:1](=[S:3])=[S:2].[CH2:4]([O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][C:8]=1[F:14])[CH3:5].[CH2:15](N(CC)CC)C.CI.Cl>CN(C)C=O>[CH2:4]([O:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][C:1](=[S:3])[S:2][CH3:15])=[CH:9][C:8]=1[F:14])[CH3:5]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 195992054-Ethoxy-3-fluoroaniline

Product 1

HCID 19599208Methyl (4-ethoxy-3-fluorophenyl)carbamodithioateYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reference Preparation Example [Preparation of Compound (Ie)]Carbon disulfide (2.0g, 26mmol) was added to a mixture of 4-ethoxy-3-fluoroaniline (2.7 g, 17 mmol) and triethylamine (4.0 g, 40 mmol) while stirring. The mixture was stirred at room temperature for 10 hours, N,N-dimethyl-formamide (30 ml) was added thereto and methyl iodide (2.2 g, 16 mmol) was added dropwise. The mixture was stirred at room temperature for 30 minutes and dilute hydrochloric acid was added thereto, followed by extraction with diethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=4:1) to obtain methyl 4-ethoxy-3-fluorophenyldithiocarbamate (2.5 g, 10mmol) as crystals. m.p. 108.0° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 10 hours
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. extractionfollowed by extraction with diethyl ether
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-6173702138084652a2e5c7d329f4de51
Source dataset
uspto-grants-1998_08
Patent number
US05798384

Linked notes

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