Potassium Carbonate → HCID 20378252, compound

HRID 2051943Notes

Reaction equation

HRID 2051943 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.Cl[CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:28]([O:27][CH2:26][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])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137983Benzyl chloromethyl ether2×HCID 135080754,5-Diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole

Product 1

HCID 20378252HCID 20378252, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.5 g (0.01 mole) of 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole, 2.1 g (0.013 mole) benzyl chloromethyl ether, 3.6 g (0.026 mole) potassium carbonate in 25 ml DMF was stirred for 24 hours. TLC showed some starting material, so an additional 0.5 g (0.003 mole) of benzyl chloromethyl ether was added and stirring continued for another 24 hours. The mixture was poured into ice water, extracted three times with ether and the ether layers backwashed three times with water. The ether solution was dried and concentrated on a rotary evaporator. The residue was chromatographed on 200 g SilicAR CC-7, eluting with toluene to give, after recrystallization from hexane, 3.6 g (76.6%) of white product, mp 70°-70.5°.

Workup

  1. stirringstirring
  2. waitcontinued for another 24 hours
  3. extractionextracted three times with ether
  4. dry with materialThe ether solution was dried
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was chromatographed on 200 g SilicAR CC-7
  7. washeluting with toluene
  8. customto give
  9. customafter recrystallization from hexane, 3.6 g (76.6%) of white product, mp 70°-70.5°

Sources & evidence

ORD record
ord-18be0d29d43f4d2d96b1d0d4e16b15f8
Source dataset
uspto-grants-1980_01
Patent number
US04182769

Reaction notes

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