Triethylamine → HCID 20378258, compound

HRID 2051955Notes

Reaction equation

HRID 2051955 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(N(CC)CC)C.Cl[CH:33]1[CH2:37][CH2:36][CH2:35][O:34]1.S(Cl)(Cl)(=O)=O>O1CCCC1>[C:12]1([C:11]2[N:10]=[C:9]([S:18][C:19]([F:23])([F:24])[CH:20]([F:22])[F:21])[N:8]([CH:33]3[CH2:37][CH2:36][CH2:35][O:34]3)[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 178730Furan, 2-chlorotetrahydro-HCID 135080754,5-Diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole

Product 1

HCID 20378258HCID 20378258, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1.8 g (0.005 mole) of 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole and 5 g (0.05 mole) triethylamine in 20 ml tetrahydrofuran, was added dropwise at room temperature a solution of 2-chlorotetrahydrofuran, which had been prepared by adding 2.4 g (0.018 mole) of sulfuryl chloride to 30 ml tetrahydrofuran and waiting until the exothermic reaction mixture had returned to room temperature. The reaction mixture was stirred at room temperature for four days, then poured into ice water containing excess sodium bicarbonate. The aqueous mixture was extracted with methylene chloride, which was dried and concentrated. The crystalline residue was purified by chromatography on silica gel, eluting with toluene, to give 1.6 g of product, mp 145°-6° (from methylcyclohexane).

Workup

  1. customhad been prepared
  2. waitwaiting until the exothermic reaction mixture
  3. customhad returned to room temperature
  4. extractionThe aqueous mixture was extracted with methylene chloride, which
  5. customwas dried
  6. concentrationconcentrated
  7. customThe crystalline residue was purified by chromatography on silica gel
  8. washeluting with toluene

Sources & evidence

ORD record
ord-08061192d6ed46a7a1a2a32db650e343
Source dataset
uspto-grants-1980_01
Patent number
US04182769

Reaction notes

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