Water → HCID 13508159, compound

HRID 1449402Notes

Reaction equation

HRID 1449402 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][N:10](C3CCCCO3)[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])CCC.[F:29][C:30]([F:34])([F:33])[S:31]Cl.O>C1COCC1.CCOCC.CCCCCC>[C:1]1([C:7]2[N:8]=[C:9]([S:31][C:30]([F:34])([F:33])[F:29])[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

Participants

8

Reactant 4

HCID 962WaterHCID 67900Methanesulfenyl chloride, trifluoro-HCID 135081561-(Oxan-2-yl)-4,5-diphenyl-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 13508159HCID 13508159, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Under nitrogen and in glassware dried with a heat gun, a solution of 0.9 g (3 mmole) of 4,5-diphenyl-1-(2-tetrahydropyranyl)imidazole in 15 ml THF and 15 ml ether was chilled to -78° C. To the cold solution was added dropwise a solution of 2.5 ml (4 mmole) of 1.6 M n-butyl lithium in hexane in 10 ml ether. The solution was stirred at -78° C., then 0.55 g (4 mmole) of trifluoromethanesulfenyl chloride (TOXIC) was added as a gas. The mixture was stirred at -78° C. for 2 hours, then at RT overnight. The mixture was poured into water and extracted with ether (pH of aqueous layer ~4). The aqueous layer was neutralized with bicarbonate then extracted with more ether. The combined ether extracts were dried and concentrated. The crude residue was chromatographed on 50 g SilicAR CC-7, eluting with 98% toluene/2% ethyl acetate, to give 0.45 g (47%) of product. Recrystallization from toluene gave 0.3 g (31%) of white solid, mp 254°-6°. ; Anal. Calc'd. for C16H11F3N2S: C, 59.99; H, 3.46; N, 8.75. Found: C, 60.20; H, 3,57; N, 8.52.

Workup

  1. customUnder nitrogen and in glassware dried with a heat gun
  2. stirringThe mixture was stirred at -78° C. for 2 hours
  3. customat RT
  4. customovernight
  5. extractionextracted with ether (pH of aqueous layer ~4)
  6. extractionthen extracted with more ether
  7. dry with materialThe combined ether extracts were dried
  8. concentrationconcentrated
  9. customThe crude residue was chromatographed on 50 g SilicAR CC-7
  10. washeluting with 98% toluene/2% ethyl acetate

Sources & evidence

ORD record
ord-22c397b47e9f4f81b02132cb6914ecd5
Source dataset
uspto-grants-1980_02
Patent number
US04190666

Reaction notes

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