Potassium Carbonate → HCID 20378255, compound

HRID 2051945Notes

Reaction equation

HRID 2051945 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18]([C:21]([F:26])([F:25])[CH:22]([F:24])[F:23])(=[O:20])=[O:19])[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[CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:30]([O:29][CH2:28][N:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]1[S:18]([C:21]([F:25])([F:26])[CH:22]([F:24])[F:23])(=[O:20])=[O:19])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137983Benzyl chloromethyl etherHCID 13508112HCID 13508112, compound

Product 1

HCID 20378255HCID 20378255, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.92 g (5 mmole) of 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole, 1.6 g (10 mmole) of benzyl chloromethyl ether, 2.8 g (20 mmole) of potassium carbonate in 20 ml DMF was stirred at RT for six hours, then poured into ice water. The aqueous mixture was extracted three times with ether. The ether extracts were backwashed three times with water, then dried and concentrated. The residue was chromatographed on 150 g SilicAR CC-7, eluting with toluene to give, after recrystallization from hexane, 2.5 g (100%) of white product, mp 97.5°-98.5°.

Workup

  1. extractionThe aqueous mixture was extracted three times with ether
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was chromatographed on 150 g SilicAR CC-7
  5. washeluting with toluene
  6. customto give
  7. customafter recrystallization from hexane, 2.5 g (100%) of white product, mp 97.5°-98.5°

Sources & evidence

ORD record
ord-7d2805ed3eaf476ea3727ecf7a1bd466
Source dataset
uspto-grants-1980_01
Patent number
US04182769

Reaction notes

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