Dimethylthiocarbamoyl chloride → HCID 20378260, compound

HRID 2051949Notes

Reaction equation

HRID 2051949 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][C:19]([F:24])([F:23])[CH:20]([F:22])[F:21])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Li].[CH3:27][N:28]([CH3:32])[C:29](Cl)=[S:30]>C1COCC1>[CH3:27][N:28]([CH3:32])[C:29]([N:10]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[C:9]1[S:18][C:19]([F:23])([F:24])[CH:20]([F:22])[F:21])=[S:30]

Participants

5

Reactant 3

HCID 27871Dimethylthiocarbamoyl chlorideHCID 135080754,5-Diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazoleHCID 178418348HCID 178418348, compound

Product 1

HCID 20378260HCID 20378260, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.0 g (0.014 mole) of 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole in 50 ml of THF was added dropwise 15 ml of 1.6 M methyl lithium solution, followed by a solution of 5.5 g (0.045 mole) of dimethylthiocarbamoyl chloride in 25 ml THF. The reaction mixture was heated at reflux several hours, then concentrated by rotary evaporation. The residue was shaken with ether and 1 N hydrochloric acid. The ether layer was washed with 10% sodium bicarbonate solution, then dried and concentrated. The residue (7.8 g) was purified by chromatography on silica gel, eluting with toluene to give 0.8 g of product, mp 133°-133.5° (recrystallized from methyl cyclohexane).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux several hours
  3. concentrationconcentrated by rotary evaporation
  4. washThe ether layer was washed with 10% sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue (7.8 g) was purified by chromatography on silica gel
  8. washeluting with toluene
  9. customto give
  10. custom0.8 g of product, mp 133°-133.5° (recrystallized from methyl cyclohexane)

Sources & evidence

ORD record
ord-5c5e53aa290342a786fe04d82d29eaec
Source dataset
uspto-grants-1980_01
Patent number
US04182769

Reaction notes

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