Triethylamine → 1-methoxycarbonylthio-1-(2-trifluoromethylbenzoyl)-2-(N,N-dimethylamino)ethene

HRID 1653887Notes

Reaction equation

HRID 1653887 reaction equation
[CH3:1][N:2]([CH:4]=[CH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14])[CH3:3].C(N(CC)CC)C.[CH3:25][O:26][C:27]([S:29]Cl)=[O:28]>C1C=CC=CC=1>[CH3:25][O:26][C:27]([S:29][C:5]([C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14])=[CH:4][N:2]([CH3:3])[CH3:1])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123417Thiocarbonic acid, anhydrosulphide with methyl thiohypochloriteHCID 542598323-(Dimethylamino)-1-[2-(trifluoromethyl)phenyl]prop-2-en-1-one

Product 1

HCID 539602891-methoxycarbonylthio-1-(2-trifluoromethylbenzoyl)-2-(N,N-dimethylamino)etheneYield 86.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

4.2 g of 1-(N,N-dimethylamino)-2-(2-trifluoromethylbenzoyl)ethene and 2.6 g of triethylamine were added to 50 ml of benzene. 2.4 g of methoxycarbonylsulfenyl chloride dissolved in 10 ml of benzene was added dropwise to the solution obtained above under cooling in an ice-bath. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled away under reduced pressure. After adding an aqueous solution of sodium hydrogencarbonate, the mixture was extracted with ether. Thus 5.0 g of 1-methoxycarbonylthio-1-(2-trifluoromethylbenzoyl)-2-(N,N-dimethylamino)ethene was obtained (Compound 209).

Workup

  1. additionwas added dropwise to the solution
  2. customobtained above
  3. temperatureunder cooling in an ice-bath
  4. additionAfter completion of the addition
  5. customAfter completion of the reaction
  6. distillationthe solvent was distilled away under reduced pressure
  7. additionAfter adding an aqueous solution of sodium hydrogencarbonate
  8. extractionthe mixture was extracted with ether

Sources & evidence

ORD record
ord-cb06592bbb14412d933a655ab2bc8b11
Source dataset
uspto-grants-1995_04
Patent number
US05403948

Reaction notes

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